GB2105327A - Novel 2-phenyl-2H-1,2,3-triazoles and their use in the preparation of fluorescent whitening agents - Google Patents
Novel 2-phenyl-2H-1,2,3-triazoles and their use in the preparation of fluorescent whitening agents Download PDFInfo
- Publication number
- GB2105327A GB2105327A GB08223111A GB8223111A GB2105327A GB 2105327 A GB2105327 A GB 2105327A GB 08223111 A GB08223111 A GB 08223111A GB 8223111 A GB8223111 A GB 8223111A GB 2105327 A GB2105327 A GB 2105327A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- formula
- c4alkyl
- substituted
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- JYBWAYHAOLQZJX-UHFFFAOYSA-N 2-phenyltriazole Chemical class N1=CC=NN1C1=CC=CC=C1 JYBWAYHAOLQZJX-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims description 14
- 239000006081 fluorescent whitening agent Substances 0.000 title abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 63
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 46
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- -1 cyano, carboxyl Chemical group 0.000 claims description 40
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 239000007858 starting material Substances 0.000 claims description 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 150000002923 oximes Chemical class 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000003863 ammonium salts Chemical class 0.000 claims description 13
- ZCYGMFCBXFGAKO-UHFFFAOYSA-N 2-(2-phenyltriazol-4-yl)acetic acid Chemical compound N1=C(CC(=O)O)C=NN1C1=CC=CC=C1 ZCYGMFCBXFGAKO-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000003852 triazoles Chemical class 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
- 238000007796 conventional method Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- XTNOKNYTEJIHIJ-UHFFFAOYSA-N 2-(2-phenyltriazol-4-yl)ethanethioamide Chemical compound C1(=CC=CC=C1)N1N=CC(=N1)CC(=S)N XTNOKNYTEJIHIJ-UHFFFAOYSA-N 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 150000008065 acid anhydrides Chemical group 0.000 claims description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- ZFSTUUVWJCYEFW-UHFFFAOYSA-N ethane;sulfurochloridic acid Chemical compound CC.OS(Cl)(=O)=O ZFSTUUVWJCYEFW-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 claims description 2
- ZOSOTVABWBBHEH-UHFFFAOYSA-N N-[bis(2-phenyltriazol-4-yl)methylidene]hydroxylamine Chemical compound C1(=CC=CC=C1)N1N=CC(=N1)C(=NO)C1=NN(N=C1)C1=CC=CC=C1 ZOSOTVABWBBHEH-UHFFFAOYSA-N 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 13
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- DMYSACQRTCVMGV-UHFFFAOYSA-N 3-oxo-2-phenyldiazenylbutanal Chemical compound C1(=CC=CC=C1)N=NC(C=O)C(C)=O DMYSACQRTCVMGV-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UKGZSRRTSPMNBH-UHFFFAOYSA-N 1-(2-phenyltriazol-4-yl)ethanone Chemical class CC(=O)C1=NN(N=C1)C1=CC=CC=C1 UKGZSRRTSPMNBH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- JQOBHNOTCOASJO-UHFFFAOYSA-N 4-hydroxyimino-3-phenyldiazenylbutan-2-one Chemical compound C1(=CC=CC=C1)N=NC(C=NO)C(=O)C JQOBHNOTCOASJO-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QUEKCNRLDNPMCA-UHFFFAOYSA-N N-[1-(2-phenyltriazol-4-yl)ethylidene]hydroxylamine Chemical compound C(C)(C1=NN(N=C1)C1=CC=CC=C1)=NO QUEKCNRLDNPMCA-UHFFFAOYSA-N 0.000 description 3
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 2
- CSQXQMPNYBDZAF-UHFFFAOYSA-N 3-hydroxyimino-1-(4-methylphenyl)-2-phenyldiazenylpropan-1-one Chemical compound O=C(C(C=NO)N=NC1=CC=CC=C1)C1=CC=C(C=C1)C CSQXQMPNYBDZAF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FXWSDNFEOXVKIY-UHFFFAOYSA-N N-(4-hydroxyimino-3-phenyldiazenylbutan-2-ylidene)hydroxylamine Chemical compound C1(=CC=CC=C1)N=NC(C=NO)C(C)=NO FXWSDNFEOXVKIY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QPWSKIGAQZAJKS-SNAWJCMRSA-N (e)-4-(dimethylamino)but-3-en-2-one Chemical compound CN(C)\C=C\C(C)=O QPWSKIGAQZAJKS-SNAWJCMRSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MEGPCWYKTKUKEG-UHFFFAOYSA-N 1-(2h-triazol-4-yl)ethanone Chemical class CC(=O)C=1C=NNN=1 MEGPCWYKTKUKEG-UHFFFAOYSA-N 0.000 description 1
- GHQLZTGXGWVGSI-UHFFFAOYSA-N 2-(2h-triazol-4-yl)acetic acid Chemical compound OC(=O)CC1=CNN=N1 GHQLZTGXGWVGSI-UHFFFAOYSA-N 0.000 description 1
- JODRRPJMQDFCBJ-UHFFFAOYSA-N 2-Hydroxy-4-methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(O)=C1 JODRRPJMQDFCBJ-UHFFFAOYSA-N 0.000 description 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- NHZQUEVSEFAPJU-UHFFFAOYSA-N 3-(4-methylphenyl)-3-oxo-2-phenyldiazenylpropanal Chemical compound O=C(C(C=O)N=NC1=CC=CC=C1)C1=CC=C(C=C1)C NHZQUEVSEFAPJU-UHFFFAOYSA-N 0.000 description 1
- SZMHSSBNDCUOON-UHFFFAOYSA-N 3-hydroxyimino-1-phenyl-2-phenyldiazenylpropan-1-one Chemical compound O=C(C(C=NO)N=NC1=CC=CC=C1)C1=CC=CC=C1 SZMHSSBNDCUOON-UHFFFAOYSA-N 0.000 description 1
- VZOPIMRGXPQUOI-UHFFFAOYSA-N 3-oxo-2-phenylbutanal Chemical compound CC(=O)C(C=O)C1=CC=CC=C1 VZOPIMRGXPQUOI-UHFFFAOYSA-N 0.000 description 1
- MHQZBZMPIJPCGY-UHFFFAOYSA-N 3-oxo-3-phenyl-2-phenyldiazenylpropanal Chemical compound O=C(C(C=O)N=NC1=CC=CC=C1)C1=CC=CC=C1 MHQZBZMPIJPCGY-UHFFFAOYSA-N 0.000 description 1
- QPWSKIGAQZAJKS-UHFFFAOYSA-N 4-(dimethylamino)but-3-en-2-one Chemical compound CN(C)C=CC(C)=O QPWSKIGAQZAJKS-UHFFFAOYSA-N 0.000 description 1
- WGJUCKKFGLFZCZ-UHFFFAOYSA-N 4-hydroxyimino-3-[(4-nitrophenyl)diazenyl]butan-2-one Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)N=NC(C=NO)C(=O)C WGJUCKKFGLFZCZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- GNRWVOMGBASECC-UHFFFAOYSA-N phenyl-(2-phenyltriazol-4-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C(=N1)C=NN1C1=CC=CC=C1 GNRWVOMGBASECC-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH530281 | 1981-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2105327A true GB2105327A (en) | 1983-03-23 |
Family
ID=4291303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08223111A Withdrawn GB2105327A (en) | 1981-08-17 | 1982-08-11 | Novel 2-phenyl-2H-1,2,3-triazoles and their use in the preparation of fluorescent whitening agents |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5839658A (it) |
| BR (1) | BR8204786A (it) |
| DE (1) | DE3230200A1 (it) |
| FR (1) | FR2511367A1 (it) |
| GB (1) | GB2105327A (it) |
| IT (1) | IT1148404B (it) |
| NL (1) | NL8203209A (it) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2274661A (en) * | 1993-02-02 | 1994-08-03 | Ciba Geigy Ag | Fluorescent Whitening of paper |
| US6919363B2 (en) | 2000-03-24 | 2005-07-19 | Euro-Celtique S.A. | Aryl substituted pyrazoles, triazoles and tetrazoles, and the use thereof |
| CN114890957A (zh) * | 2022-01-25 | 2022-08-12 | 南京工业大学 | 一种三氮唑衍生物及制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3826752A (en) * | 1970-03-11 | 1974-07-30 | Ciba Geigy Corp | Protective agents against light rays |
| JPS5748552B2 (it) * | 1974-09-02 | 1982-10-16 | ||
| JPS5278873A (en) * | 1975-12-26 | 1977-07-02 | Mitsui Toatsu Chem Inc | Preparation of 2-aryl-1,2,3-triazolyl-4-acetic acids |
| GB2063876B (en) * | 1979-11-14 | 1983-12-21 | Sandoz Products Ltd | Stilbene derivatives and their use as optical brightening agents |
-
1982
- 1982-08-11 GB GB08223111A patent/GB2105327A/en not_active Withdrawn
- 1982-08-12 FR FR8214059A patent/FR2511367A1/fr active Pending
- 1982-08-12 IT IT48984/82A patent/IT1148404B/it active
- 1982-08-13 DE DE19823230200 patent/DE3230200A1/de not_active Withdrawn
- 1982-08-16 BR BR8204786A patent/BR8204786A/pt unknown
- 1982-08-16 NL NL8203209A patent/NL8203209A/nl not_active Application Discontinuation
- 1982-08-17 JP JP57141765A patent/JPS5839658A/ja active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2274661A (en) * | 1993-02-02 | 1994-08-03 | Ciba Geigy Ag | Fluorescent Whitening of paper |
| GB2274661B (en) * | 1993-02-02 | 1996-07-17 | Ciba Geigy Ag | Fluorescent whitening of paper |
| US6919363B2 (en) | 2000-03-24 | 2005-07-19 | Euro-Celtique S.A. | Aryl substituted pyrazoles, triazoles and tetrazoles, and the use thereof |
| US7078426B2 (en) | 2000-03-24 | 2006-07-18 | Euro-Celtique S.A. | Aryl substituted pyrazoles, triazoles, and tetrazoles, and the use thereof |
| CN114890957A (zh) * | 2022-01-25 | 2022-08-12 | 南京工业大学 | 一种三氮唑衍生物及制备方法 |
| CN114890957B (zh) * | 2022-01-25 | 2023-05-30 | 南京工业大学 | 一种三氮唑衍生物及制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1148404B (it) | 1986-12-03 |
| FR2511367A1 (fr) | 1983-02-18 |
| IT8248984A0 (it) | 1982-08-12 |
| NL8203209A (nl) | 1983-03-16 |
| BR8204786A (pt) | 1983-08-02 |
| JPS5839658A (ja) | 1983-03-08 |
| DE3230200A1 (de) | 1983-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |