DE1294384B - Verfahren zur Herstellung von 1-(2-Alkyl-4-amino-5-pyrimidyl-methyl)-pyridiniumhalogeniden - Google Patents
Verfahren zur Herstellung von 1-(2-Alkyl-4-amino-5-pyrimidyl-methyl)-pyridiniumhalogenidenInfo
- Publication number
- DE1294384B DE1294384B DEM47077A DEM0047077A DE1294384B DE 1294384 B DE1294384 B DE 1294384B DE M47077 A DEM47077 A DE M47077A DE M0047077 A DEM0047077 A DE M0047077A DE 1294384 B DE1294384 B DE 1294384B
- Authority
- DE
- Germany
- Prior art keywords
- amino
- pyrimidylmethyl
- methyl
- mixture
- alkyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 11
- 150000003222 pyridines Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- -1 Alkyl radical Chemical class 0.000 description 40
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 16
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
- 239000008096 xylene Substances 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 4
- GTUSSWYXAVBUEZ-UHFFFAOYSA-N 5-(methoxymethyl)-2-propylpyrimidin-4-amine Chemical compound CCCC1=NC=C(COC)C(N)=N1 GTUSSWYXAVBUEZ-UHFFFAOYSA-N 0.000 description 4
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- GGTLWUZUPFXLAI-UHFFFAOYSA-N 2-ethyl-5-(methoxymethyl)pyrimidin-4-amine Chemical compound CCC1=NC=C(COC)C(N)=N1 GGTLWUZUPFXLAI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- ZYCMDWDFIQDPLP-UHFFFAOYSA-N hbr bromine Chemical compound Br.Br ZYCMDWDFIQDPLP-UHFFFAOYSA-N 0.000 description 3
- PJBQYZZKGNOKNJ-UHFFFAOYSA-M hydron;5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine;dichloride Chemical compound Cl.[Cl-].NC1=NC(CCC)=NC=C1C[N+]1=CC=CC=C1C PJBQYZZKGNOKNJ-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- YTJVJNLOJLUUBX-UHFFFAOYSA-M 5-[(4-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine chloride hydrochloride Chemical compound Cl.[Cl-].C(CC)C1=NC=C(C(=N1)N)C[N+]1=CC=C(C=C1)C YTJVJNLOJLUUBX-UHFFFAOYSA-M 0.000 description 2
- SBXCRJQWPBDRSD-UHFFFAOYSA-M Cl.[Cl-].C(C)C1=NC=C(C(=N1)N)C[N+]1=C(C=CC=C1)C Chemical compound Cl.[Cl-].C(C)C1=NC=C(C(=N1)N)C[N+]1=C(C=CC=C1)C SBXCRJQWPBDRSD-UHFFFAOYSA-M 0.000 description 2
- 208000003495 Coccidiosis Diseases 0.000 description 2
- 206010023076 Isosporiasis Diseases 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- YXZUDXLWSOZHFN-UHFFFAOYSA-N 2,3-diethylpyridine Chemical compound CCC1=CC=CN=C1CC YXZUDXLWSOZHFN-UHFFFAOYSA-N 0.000 description 1
- ZZNHVWPSIBWAOF-UHFFFAOYSA-N 2,4-diethylpyridine Chemical compound CCC1=CC=NC(CC)=C1 ZZNHVWPSIBWAOF-UHFFFAOYSA-N 0.000 description 1
- JJWZJZCVLLJIOS-UHFFFAOYSA-N 2-ethyl-5-(propan-2-yloxymethyl)pyrimidin-4-amine Chemical compound C(C)C1=NC=C(C(=N1)N)COC(C)C JJWZJZCVLLJIOS-UHFFFAOYSA-N 0.000 description 1
- HVVIOQUVPKXZRT-UHFFFAOYSA-M 2-ethyl-5-[(2-methylpyridin-1-ium-1-yl)methyl]pyrimidin-4-amine bromide hydrobromide Chemical compound Br.[Br-].C(C)C1=NC=C(C(=N1)N)C[N+]1=C(C=CC=C1)C HVVIOQUVPKXZRT-UHFFFAOYSA-M 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- OMSBSIXAZZRIRW-UHFFFAOYSA-N 2-methylpyridine;hydrochloride Chemical compound Cl.CC1=CC=CC=N1 OMSBSIXAZZRIRW-UHFFFAOYSA-N 0.000 description 1
- LNJMHEJAYSYZKK-UHFFFAOYSA-N 2-methylpyrimidine Chemical compound CC1=NC=CC=N1 LNJMHEJAYSYZKK-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
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 description 1
- JAWZAONCXMJLFT-UHFFFAOYSA-N 4-propylpyridine Chemical compound CCCC1=CC=NC=C1 JAWZAONCXMJLFT-UHFFFAOYSA-N 0.000 description 1
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 description 1
- NQHSRVYHHWWPCZ-UHFFFAOYSA-N 5-(methoxymethyl)-2-methylpyrimidin-4-amine Chemical compound COCC1=CN=C(C)N=C1N NQHSRVYHHWWPCZ-UHFFFAOYSA-N 0.000 description 1
- CXVSULTXGLIXRN-UHFFFAOYSA-N 7-oxa-5-azabicyclo[4.1.0]hepta-1(6),2,4-triene Chemical compound C1=CN=C2OC2=C1 CXVSULTXGLIXRN-UHFFFAOYSA-N 0.000 description 1
- WUZQOZJGNLJKLH-UHFFFAOYSA-M Br.[Br-].C(CC)C1=NC=C(C(=N1)N)C[N+]1=CC=C(C=C1)C Chemical compound Br.[Br-].C(CC)C1=NC=C(C(=N1)N)C[N+]1=CC=C(C=C1)C WUZQOZJGNLJKLH-UHFFFAOYSA-M 0.000 description 1
- NDFFZJFKHZTSEV-UHFFFAOYSA-M Br.[Br-].CC1=NC=C(C(=N1)N)C[N+]1=C(C=CC=C1)C Chemical compound Br.[Br-].CC1=NC=C(C(=N1)N)C[N+]1=C(C=CC=C1)C NDFFZJFKHZTSEV-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- PWWSPSQHDUVATA-UHFFFAOYSA-N Cl.C(CC)C1=NC=C(C(=N1)N)COC Chemical compound Cl.C(CC)C1=NC=C(C(=N1)N)COC PWWSPSQHDUVATA-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 208000027954 Poultry disease Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- AINXPKWJTYREPA-UHFFFAOYSA-M [2-methyl-5-[(2-methylpyridin-1-ium-1-yl)methyl]pyrimidin-4-yl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=[NH+]C(C)=NC(N)=C1C[N+]1=CC=CC=C1C AINXPKWJTYREPA-UHFFFAOYSA-M 0.000 description 1
- CLWRFNUKIFTVHQ-UHFFFAOYSA-N [N].C1=CC=NC=C1 Chemical group [N].C1=CC=NC=C1 CLWRFNUKIFTVHQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000021178 picnic Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85427459A | 1959-11-20 | 1959-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1294384B true DE1294384B (de) | 1969-05-08 |
Family
ID=25318217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM47077A Pending DE1294384B (de) | 1959-11-20 | 1960-11-08 | Verfahren zur Herstellung von 1-(2-Alkyl-4-amino-5-pyrimidyl-methyl)-pyridiniumhalogeniden |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE597062A (xx) |
| CH (1) | CH389606A (xx) |
| DE (1) | DE1294384B (xx) |
| DK (1) | DK115259B (xx) |
| ES (1) | ES262980A1 (xx) |
| FI (1) | FI44402B (xx) |
| GB (1) | GB911552A (xx) |
| NL (1) | NL257970A (xx) |
| SE (1) | SE309777B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795071A (fr) * | 1972-02-08 | 1973-08-07 | Merck & Co Inc | Composes coccidiostatiques |
| CN110981855B (zh) * | 2019-12-09 | 2020-10-30 | 浙江大洋生物科技集团股份有限公司 | 高残渣盐酸氨丙啉的提纯方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB522531A (xx) * | 1900-01-01 | |||
| US2587262A (en) * | 1952-02-26 | Chs chzghjoh |
-
0
- NL NL257970D patent/NL257970A/xx unknown
- BE BE597062D patent/BE597062A/xx unknown
-
1960
- 1960-11-08 DE DEM47077A patent/DE1294384B/de active Pending
- 1960-11-10 FI FI1840/60A patent/FI44402B/fi active
- 1960-11-10 GB GB38676/60A patent/GB911552A/en not_active Expired
- 1960-11-18 CH CH1296560A patent/CH389606A/de unknown
- 1960-11-19 DK DK461060A patent/DK115259B/da unknown
- 1960-11-19 ES ES0262980A patent/ES262980A1/es not_active Expired
- 1960-11-21 SE SE11229/60A patent/SE309777B/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB522531A (xx) * | 1900-01-01 | |||
| US2587262A (en) * | 1952-02-26 | Chs chzghjoh |
Also Published As
| Publication number | Publication date |
|---|---|
| BE597062A (xx) | |
| CH389606A (de) | 1965-03-31 |
| NL257970A (xx) | |
| FI44402B (xx) | 1971-08-02 |
| SE309777B (xx) | 1969-04-08 |
| GB911552A (en) | 1962-11-28 |
| DK115259B (da) | 1969-09-22 |
| ES262980A1 (es) | 1961-02-01 |
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