CH621772A5 - - Google Patents
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- Publication number
- CH621772A5 CH621772A5 CH914776A CH914776A CH621772A5 CH 621772 A5 CH621772 A5 CH 621772A5 CH 914776 A CH914776 A CH 914776A CH 914776 A CH914776 A CH 914776A CH 621772 A5 CH621772 A5 CH 621772A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- cyanimino
- propionitrile
- formula
- alkyl radicals
- Prior art date
Links
- -1 Triaminopyrimidine N-oxides Chemical class 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 14
- KTZUXSWSWXTCQG-UHFFFAOYSA-N n,2-dicyanoacetamide Chemical compound N#CCC(=O)NC#N KTZUXSWSWXTCQG-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 8
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 7
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- WJESXAYAUFUJEI-UHFFFAOYSA-N 2-cyanoethylidenecyanamide Chemical compound N#CCC=NC#N WJESXAYAUFUJEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- JZZUKPAAFVSBJA-UHFFFAOYSA-N NC1=CC(N)=[N+]([O-])C(N)=N1 Chemical compound NC1=CC(N)=[N+]([O-])C(N)=N1 JZZUKPAAFVSBJA-UHFFFAOYSA-N 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000005554 pickling Methods 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 239000003223 protective agent Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- FDXSJSYTFLRXGI-UHFFFAOYSA-N ethyl n,2-dicyanoethanimidate Chemical compound CCOC(CC#N)=NC#N FDXSJSYTFLRXGI-UHFFFAOYSA-N 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical class N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DWJCWLQCJCJTLL-UHFFFAOYSA-N (2-cyano-1-morpholin-4-ylethylidene)cyanamide Chemical compound N#CCC(=NC#N)N1CCOCC1 DWJCWLQCJCJTLL-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- UMXADXYSYVKRJV-UHFFFAOYSA-N ethyl 2-cyanoethanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CC#N UMXADXYSYVKRJV-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- NFBYUVCAJNYCEG-UHFFFAOYSA-N n',2-dicyanoethanimidamide Chemical compound N#CCC(N)=NC#N NFBYUVCAJNYCEG-UHFFFAOYSA-N 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- YPADUFXSRCGIHX-UHFFFAOYSA-N (2-cyano-1-piperidin-1-ylbut-3-enylidene)cyanamide Chemical compound C=CC(C#N)C(=NC#N)N1CCCCC1 YPADUFXSRCGIHX-UHFFFAOYSA-N 0.000 description 1
- IYZAGWDRJMCFDI-UHFFFAOYSA-N (2-cyano-1-piperidin-1-ylbutylidene)cyanamide Chemical compound CCC(C#N)C(=NC#N)N1CCCCC1 IYZAGWDRJMCFDI-UHFFFAOYSA-N 0.000 description 1
- GKKYXKYZPZXNOG-UHFFFAOYSA-N (2-cyano-1-piperidin-1-ylheptylidene)cyanamide Chemical compound CCCCCC(C#N)C(=NC#N)N1CCCCC1 GKKYXKYZPZXNOG-UHFFFAOYSA-N 0.000 description 1
- UHSXYTPZHDYEDA-UHFFFAOYSA-N (2-cyano-1-piperidin-1-ylhexylidene)cyanamide Chemical compound CCCCC(C#N)C(=NC#N)N1CCCCC1 UHSXYTPZHDYEDA-UHFFFAOYSA-N 0.000 description 1
- FITDWLKJSCSDKU-UHFFFAOYSA-N (2-cyano-1-piperidin-1-yloct-5-enylidene)cyanamide Chemical compound CCC=CCCC(C#N)C(=NC#N)N1CCCCC1 FITDWLKJSCSDKU-UHFFFAOYSA-N 0.000 description 1
- MEVVPNHVFPUOFU-UHFFFAOYSA-N (2-cyano-1-piperidin-1-yloctylidene)cyanamide Chemical compound CCCCCCC(C#N)C(=NC#N)N1CCCCC1 MEVVPNHVFPUOFU-UHFFFAOYSA-N 0.000 description 1
- YHVLVUVUVPOUAK-UHFFFAOYSA-N (2-cyano-1-piperidin-1-ylpentylidene)cyanamide Chemical compound CCCC(C#N)C(=NC#N)N1CCCCC1 YHVLVUVUVPOUAK-UHFFFAOYSA-N 0.000 description 1
- YKBZRBPMFDENGB-UHFFFAOYSA-N (2-cyano-1-piperidin-1-ylpropylidene)cyanamide Chemical compound N#CC(C)C(=NC#N)N1CCCCC1 YKBZRBPMFDENGB-UHFFFAOYSA-N 0.000 description 1
- DSWFBAZNNGSGOP-UHFFFAOYSA-N (2-cyano-1-pyrrolidin-1-ylethylidene)cyanamide Chemical compound N#CCC(=NC#N)N1CCCC1 DSWFBAZNNGSGOP-UHFFFAOYSA-N 0.000 description 1
- VPEVCNQQNQQAHV-UHFFFAOYSA-N (2-cyano-2-cycloheptyl-1-piperidin-1-ylethylidene)cyanamide Chemical compound C1CCCCN1C(=NC#N)C(C#N)C1CCCCCC1 VPEVCNQQNQQAHV-UHFFFAOYSA-N 0.000 description 1
- QQAMUKQJHJOUSP-UHFFFAOYSA-N (2-cyano-2-cyclohexyl-1-piperidin-1-ylethylidene)cyanamide Chemical compound C1CCCCN1C(=NC#N)C(C#N)C1CCCCC1 QQAMUKQJHJOUSP-UHFFFAOYSA-N 0.000 description 1
- WRKYQGQDZNVFLN-UHFFFAOYSA-N (2-cyano-2-cyclopentyl-1-piperidin-1-ylethylidene)cyanamide Chemical compound C1CCCCN1C(=NC#N)C(C#N)C1CCCC1 WRKYQGQDZNVFLN-UHFFFAOYSA-N 0.000 description 1
- FEVYOQKFRKZLGN-UHFFFAOYSA-N (2-cyano-3,3-dimethyl-1-piperidin-1-ylbutylidene)cyanamide Chemical compound CC(C)(C)C(C#N)C(=NC#N)N1CCCCC1 FEVYOQKFRKZLGN-UHFFFAOYSA-N 0.000 description 1
- JHRQXEZKPVXLAS-UHFFFAOYSA-N (2-cyano-3-phenyl-1-piperidin-1-ylheptylidene)cyanamide Chemical compound C=1C=CC=CC=1C(CCCC)C(C#N)C(=NC#N)N1CCCCC1 JHRQXEZKPVXLAS-UHFFFAOYSA-N 0.000 description 1
- XPWOEROAYXDBKF-UHFFFAOYSA-N (2-cyano-3-phenyl-1-piperidin-1-ylpropylidene)cyanamide Chemical compound C1CCCCN1C(=NC#N)C(C#N)CC1=CC=CC=C1 XPWOEROAYXDBKF-UHFFFAOYSA-N 0.000 description 1
- HUGDZTKVVIZHMO-UHFFFAOYSA-N (2-cyano-4-methyl-1-piperidin-1-ylpent-3-enylidene)cyanamide Chemical compound CC(C)=CC(C#N)C(=NC#N)N1CCCCC1 HUGDZTKVVIZHMO-UHFFFAOYSA-N 0.000 description 1
- UWRAULHINBGOLP-UHFFFAOYSA-N (2-cyano-4-phenyl-1-piperidin-1-ylbutylidene)cyanamide Chemical compound C1CCCCN1C(=NC#N)C(C#N)CCC1=CC=CC=C1 UWRAULHINBGOLP-UHFFFAOYSA-N 0.000 description 1
- OKSREYFZWLUOIH-UHFFFAOYSA-N (2-cyano-4-phenyl-1-piperidin-1-ylpentylidene)cyanamide Chemical compound C=1C=CC=CC=1C(C)CC(C#N)C(=NC#N)N1CCCCC1 OKSREYFZWLUOIH-UHFFFAOYSA-N 0.000 description 1
- JTJDJKSQWSLGCM-UHFFFAOYSA-N (2-cyano-5-methyl-1-piperidin-1-ylhexylidene)cyanamide Chemical compound CC(C)CCC(C#N)C(=NC#N)N1CCCCC1 JTJDJKSQWSLGCM-UHFFFAOYSA-N 0.000 description 1
- MTJIHPWPRWUWBO-UHFFFAOYSA-N (2-cyano-5-phenyl-1-piperidin-1-yloctylidene)cyanamide Chemical compound C=1C=CC=CC=1C(CCC)CCC(C#N)C(=NC#N)N1CCCCC1 MTJIHPWPRWUWBO-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- UZOVIHCILYKHPQ-UHFFFAOYSA-N 1,3-diethylpiperazine Chemical compound CCC1CN(CC)CCN1 UZOVIHCILYKHPQ-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- QOZOFODNIBQPGN-UHFFFAOYSA-N 2,4-dimethylpiperidine Chemical compound CC1CCNC(C)C1 QOZOFODNIBQPGN-UHFFFAOYSA-N 0.000 description 1
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
- VTMAUZYMCFKATR-UHFFFAOYSA-N 2-cyanoacetamide;hydrochloride Chemical compound Cl.OC(=N)CC#N VTMAUZYMCFKATR-UHFFFAOYSA-N 0.000 description 1
- DLBWPRNUXWYLRN-UHFFFAOYSA-N 2-methylazetidine Chemical compound CC1CCN1 DLBWPRNUXWYLRN-UHFFFAOYSA-N 0.000 description 1
- 125000003890 2-phenylbutyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- DZFFQSFNUBWNSF-UHFFFAOYSA-N 3-ethylpyrrolidine Chemical compound CCC1CCNC1 DZFFQSFNUBWNSF-UHFFFAOYSA-N 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- HIQFZWRIYXHUMX-UHFFFAOYSA-N [2-cyano-1-(3,4-diethylpiperazin-1-yl)ethylidene]cyanamide Chemical compound CCC1CN(C(CC#N)=NC#N)CCN1CC HIQFZWRIYXHUMX-UHFFFAOYSA-N 0.000 description 1
- IAJRRHAULGTDSY-UHFFFAOYSA-N [2-cyano-1-(3,5-dipropylpiperazin-1-yl)ethylidene]cyanamide Chemical compound CCCC1CN(C(CC#N)=NC#N)CC(CCC)N1 IAJRRHAULGTDSY-UHFFFAOYSA-N 0.000 description 1
- XMVUWQZZLYKBQY-UHFFFAOYSA-N [2-cyano-1-(3-methylmorpholin-4-yl)ethylidene]cyanamide Chemical compound CC1COCCN1C(CC#N)=NC#N XMVUWQZZLYKBQY-UHFFFAOYSA-N 0.000 description 1
- VKEAAZMWYKUVQW-UHFFFAOYSA-N [2-cyano-2-(2-methylcyclohexyl)-1-piperidin-1-ylethylidene]cyanamide Chemical compound CC1CCCCC1C(C#N)C(=NC#N)N1CCCCC1 VKEAAZMWYKUVQW-UHFFFAOYSA-N 0.000 description 1
- KNLXTEXAGUCVFC-UHFFFAOYSA-N [2-cyano-2-(4,4-dimethylcyclohexyl)-1-piperidin-1-ylethylidene]cyanamide Chemical compound C1CC(C)(C)CCC1C(C#N)C(=NC#N)N1CCCCC1 KNLXTEXAGUCVFC-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
- KMYOVZAMFRPSIX-UHFFFAOYSA-N butyl n,2-dicyano-2-cyclohexylethanimidate Chemical compound CCCCOC(=NC#N)C(C#N)C1CCCCC1 KMYOVZAMFRPSIX-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- IUNDGBLHPVEPLD-UHFFFAOYSA-N ethyl n,2-dicyanopentanimidate Chemical compound CCCC(C#N)C(OCC)=NC#N IUNDGBLHPVEPLD-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- HMNHKDNKZFSVNC-UHFFFAOYSA-N n',2-dicyano-n,n-diethylethanimidamide Chemical compound CCN(CC)C(CC#N)=NC#N HMNHKDNKZFSVNC-UHFFFAOYSA-N 0.000 description 1
- BLLNLIXPFRLWJV-UHFFFAOYSA-N n',2-dicyano-n,n-diethylpentanimidamide Chemical compound CCCC(C#N)C(=NC#N)N(CC)CC BLLNLIXPFRLWJV-UHFFFAOYSA-N 0.000 description 1
- BYTCZMCAUULOOX-UHFFFAOYSA-N n',2-dicyano-n-cyclohexyl-n-ethylethanimidamide Chemical compound N#CCC(=NC#N)N(CC)C1CCCCC1 BYTCZMCAUULOOX-UHFFFAOYSA-N 0.000 description 1
- FKTFQLURDJMLBX-UHFFFAOYSA-N n',2-dicyano-n-ethenyl-n-methylethanimidamide Chemical compound C=CN(C)C(CC#N)=NC#N FKTFQLURDJMLBX-UHFFFAOYSA-N 0.000 description 1
- FOIYPJMFPRFCHO-UHFFFAOYSA-N n',2-dicyano-n-ethyl-n-methylethanimidamide Chemical compound CCN(C)C(CC#N)=NC#N FOIYPJMFPRFCHO-UHFFFAOYSA-N 0.000 description 1
- KNXBEJDAROYSPI-UHFFFAOYSA-N n',2-dicyano-n-hexyl-n-octylethanimidamide Chemical compound CCCCCCCCN(C(CC#N)=NC#N)CCCCCC KNXBEJDAROYSPI-UHFFFAOYSA-N 0.000 description 1
- DOKVNVOIDDYUCN-UHFFFAOYSA-N n',2-dicyano-n-methyl-n-(2-methylpropyl)ethanimidamide Chemical compound CC(C)CN(C)C(CC#N)=NC#N DOKVNVOIDDYUCN-UHFFFAOYSA-N 0.000 description 1
- BLEAJGGUNNDYSX-UHFFFAOYSA-N n,2-dicyano-n'-(2-phenylbutyl)ethanimidamide Chemical compound N#CCC(NC#N)=NCC(CC)C1=CC=CC=C1 BLEAJGGUNNDYSX-UHFFFAOYSA-N 0.000 description 1
- MVOQRKCYTOZGFY-UHFFFAOYSA-N n,2-dicyano-n'-(3-methylcyclopentyl)ethanimidamide Chemical compound CC1CCC(NC(CC#N)=NC#N)C1 MVOQRKCYTOZGFY-UHFFFAOYSA-N 0.000 description 1
- RLOIIJQVLHXGLT-UHFFFAOYSA-N n,2-dicyano-n'-(3-phenylpentyl)ethanimidamide Chemical compound N#CCC(NC#N)=NCCC(CC)C1=CC=CC=C1 RLOIIJQVLHXGLT-UHFFFAOYSA-N 0.000 description 1
- UPECVLFXAHHOMT-UHFFFAOYSA-N n,2-dicyano-n'-cyclooctylethanimidamide Chemical compound N#CCC(=NC#N)NC1CCCCCCC1 UPECVLFXAHHOMT-UHFFFAOYSA-N 0.000 description 1
- YRJWRNLIFNFMBC-UHFFFAOYSA-N n,2-dicyano-n'-cyclopentyl-3-phenylpropanimidamide Chemical compound C=1C=CC=CC=1CC(C#N)C(=NC#N)NC1CCCC1 YRJWRNLIFNFMBC-UHFFFAOYSA-N 0.000 description 1
- LMZCPNDFWZGIKR-UHFFFAOYSA-N n,2-dicyano-n'-cyclopentylethanimidamide Chemical compound N#CCC(=NC#N)NC1CCCC1 LMZCPNDFWZGIKR-UHFFFAOYSA-N 0.000 description 1
- ZUAAWCBTCAMKDS-UHFFFAOYSA-N n,2-dicyano-n'-heptylethanimidamide Chemical compound CCCCCCCNC(CC#N)=NC#N ZUAAWCBTCAMKDS-UHFFFAOYSA-N 0.000 description 1
- OXRAWAJLWFVGTP-UHFFFAOYSA-N n-butyl-n',2-dicyano-n-prop-2-enylethanimidamide Chemical compound CCCCN(CC=C)C(CC#N)=NC#N OXRAWAJLWFVGTP-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/599,912 US4032559A (en) | 1975-07-28 | 1975-07-28 | N,2-dicyanoacetimidates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621772A5 true CH621772A5 (fr) | 1981-02-27 |
Family
ID=24401623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH914776A CH621772A5 (fr) | 1975-07-28 | 1976-07-16 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4032559A (fr) |
| JP (1) | JPS5949225B2 (fr) |
| CA (1) | CA1060443A (fr) |
| CH (1) | CH621772A5 (fr) |
| DK (1) | DK324776A (fr) |
| HU (1) | HU176897B (fr) |
| MX (1) | MX3223E (fr) |
| SE (3) | SE424547B (fr) |
| SU (1) | SU786889A3 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS545608B2 (fr) * | 1973-12-04 | 1979-03-19 | ||
| JPS5312776Y2 (fr) * | 1976-10-01 | 1978-04-06 | ||
| US4098791A (en) * | 1977-07-29 | 1978-07-04 | The Upjohn Company | Process for preparing 3-(cyanimino)-3-amino-propionitriles |
| DE2860431D1 (en) * | 1977-10-27 | 1981-02-26 | Basf Ag | Alpha-aminomethylene-beta-formylaminopropionitrile, process for its preparation and its use in the preparation of 2-methyl-4-amino-5-formylaminomethylpyrimidine |
| CH637153A5 (de) * | 1978-06-02 | 1983-07-15 | Ciba Geigy Ag | Azofarbstoffe und verfahren zur herstellung von azofarbstoffen. |
| AR225772A1 (es) * | 1979-08-14 | 1982-04-30 | Du Pont | Nuevo 3-amino-3-alcoxi-n-ciano-2-propenimidato de alquilo y procedimientos para su preparacion y de pirimidinas partiendo de aquellos |
| US4308271A (en) * | 1980-06-23 | 1981-12-29 | The Upjohn Company | Animal feed and process |
| US4515626A (en) * | 1982-10-06 | 1985-05-07 | Ciba Geigy Corporation | N-(Cyclopropyl-triazinyl-n'-(arylsulfonyl) ureas having herbicidal activity |
| DE3642832A1 (de) * | 1986-12-16 | 1988-06-30 | Hoechst Ag | Verfahren zur herstellung von aminopyrimidinen |
| DE3642830A1 (de) * | 1986-12-16 | 1988-07-07 | Hoechst Ag | Verfahren zur herstellung von pyrimidinen |
| FR2671082B1 (fr) * | 1990-12-28 | 1993-04-16 | Oreal | Agent a plusieurs composants ou kit de preparation de la forme sulfo-conjuguee de composes pyrimidino- ou triazino-n-oxyde et procede de mise en óoeuvre. |
| CN107879950B (zh) * | 2017-10-13 | 2020-05-08 | 中国石油天然气股份有限公司 | 一种n’-长链烷基-n,n-二乙基乙脒及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3068274A (en) * | 1960-08-18 | 1962-12-11 | Eastman Kodak Co | (2-cyano-3-amino)thio-2-alkenamides |
| US3291827A (en) * | 1963-03-05 | 1966-12-13 | American Cyanamid Co | Process for preparing n, n'-dicyanoamidine salts |
| US3225077A (en) * | 1963-03-05 | 1965-12-21 | American Cyanamid Co | N-cyanoimidates and processes for preparing same |
| US3641103A (en) * | 1969-06-03 | 1972-02-08 | Grace W R & Co | Process for preparing amidine salts |
| US3910928A (en) * | 1974-04-26 | 1975-10-07 | Upjohn Co | 3-(Cyanimino)-propionitriles |
| US3948915A (en) * | 1974-07-08 | 1976-04-06 | Daiichi Seiyaku, Co., Ltd. | 2-Halopyrimidine derivatives and a method for their preparation |
-
1975
- 1975-07-28 US US05/599,912 patent/US4032559A/en not_active Expired - Lifetime
-
1976
- 1976-06-15 CA CA254,875A patent/CA1060443A/fr not_active Expired
- 1976-06-16 MX MX000317U patent/MX3223E/es unknown
- 1976-07-13 JP JP51082626A patent/JPS5949225B2/ja not_active Expired
- 1976-07-16 SE SE7608162A patent/SE424547B/xx not_active IP Right Cessation
- 1976-07-16 CH CH914776A patent/CH621772A5/de not_active IP Right Cessation
- 1976-07-19 DK DK324776A patent/DK324776A/da not_active Application Discontinuation
- 1976-07-27 SU SU762386153A patent/SU786889A3/ru active
- 1976-07-28 HU HU76UO122A patent/HU176897B/hu unknown
-
1982
- 1982-03-30 SE SE8202034A patent/SE8202034L/xx not_active Application Discontinuation
- 1982-03-30 SE SE8202033A patent/SE8202033L/sv not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HU176897B (en) | 1981-05-28 |
| JPS5214726A (en) | 1977-02-03 |
| SE424547B (sv) | 1982-07-26 |
| US4032559A (en) | 1977-06-28 |
| SU786889A3 (ru) | 1980-12-07 |
| CA1060443A (fr) | 1979-08-14 |
| DK324776A (da) | 1977-01-29 |
| SE8202033L (sv) | 1982-03-30 |
| SE8202034L (sv) | 1982-03-30 |
| SE7608162L (sv) | 1977-01-29 |
| MX3223E (es) | 1980-07-28 |
| JPS5949225B2 (ja) | 1984-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |