HU195183B - Process for producing alpha-(o-chlorphenyl)-aminomethylene-beta-formilamino-propionitrile - Google Patents
Process for producing alpha-(o-chlorphenyl)-aminomethylene-beta-formilamino-propionitrile Download PDFInfo
- Publication number
- HU195183B HU195183B HU853211A HU321185A HU195183B HU 195183 B HU195183 B HU 195183B HU 853211 A HU853211 A HU 853211A HU 321185 A HU321185 A HU 321185A HU 195183 B HU195183 B HU 195183B
- Authority
- HU
- Hungary
- Prior art keywords
- mol
- reaction mixture
- added
- stirred
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000002081 enamines Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- YFGRSOGKVQIGKG-UHFFFAOYSA-N [Cl].NC1=CC=CC=C1 Chemical compound [Cl].NC1=CC=CC=C1 YFGRSOGKVQIGKG-UHFFFAOYSA-N 0.000 claims 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical class NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- PVWNFAGYFUUDRC-UHFFFAOYSA-N 4-amino-5-formamidomethyl-2-methylpyrimidine Chemical compound CC1=NC=C(CNC=O)C(N)=N1 PVWNFAGYFUUDRC-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 150000003230 pyrimidines Chemical class 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- -1 α-amino methylene-β-formylaminopropionitrile Chemical class 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical group CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BXHGNAADUUXBKK-UHFFFAOYSA-N 2-methylpyrimidine-4-carbaldehyde Chemical compound CC1=NC=CC(C=O)=N1 BXHGNAADUUXBKK-UHFFFAOYSA-N 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000004072 Panicum sumatrense Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- LWUUXENGQFMODR-UHFFFAOYSA-N n-(2-cyanoethyl)formamide Chemical compound O=CNCCC#N LWUUXENGQFMODR-UHFFFAOYSA-N 0.000 description 1
- JKCIQGDQLSBJPH-UHFFFAOYSA-N n-(4-amino-2,6-dimethylpyrimidin-5-yl)formamide Chemical compound CC1=NC(C)=C(NC=O)C(N)=N1 JKCIQGDQLSBJPH-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
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 |
|---|---|---|---|
| DE19843431270 DE3431270A1 (de) | 1984-08-25 | 1984-08-25 | Alpha-(o-chlorphenyl)-aminomethylen-beta-formylaminopropionitril, verfahren zu seiner herstellung sowie verwendung zur herstellung von 2-methyl-4-amino-5-formylaminomethylpyrimidin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT38916A HUT38916A (en) | 1986-07-28 |
| HU195183B true HU195183B (en) | 1988-04-28 |
Family
ID=6243851
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU853211A HU195183B (en) | 1984-08-25 | 1985-08-23 | Process for producing alpha-(o-chlorphenyl)-aminomethylene-beta-formilamino-propionitrile |
| HU873509A HU195785B (en) | 1984-08-25 | 1985-08-23 | Process for production of 2-methil-4-amin-5-/formilamin-methil/-piramidine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU873509A HU195785B (en) | 1984-08-25 | 1985-08-23 | Process for production of 2-methil-4-amin-5-/formilamin-methil/-piramidine |
Country Status (6)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4879422A (en) * | 1987-07-07 | 1989-11-07 | Sumitomo Chemical Company, Limited | Method for producing cycloalkanol |
| DE10142335A1 (de) * | 2001-08-30 | 2003-03-20 | Bayer Ag | N-unsubstituierte Amidinium-Salze |
| EP1972620A1 (en) * | 2007-01-19 | 2008-09-24 | DSMIP Assets B.V. | Synthesis of 4-amino-pyrimidines |
| JP5618306B2 (ja) * | 2008-07-22 | 2014-11-05 | ディーエスエム アイピー アセッツ ビー．ブイ． | 置換４−アミノ−ピリミジンの新規合成 |
| CN101948465A (zh) * | 2010-08-25 | 2011-01-19 | 江苏兄弟维生素有限公司 | 一种制备维生素b1中间体的方法 |
| CN103012282B (zh) * | 2012-12-03 | 2015-04-22 | 华中药业股份有限公司 | 一种维生素b1中间体的合成方法 |
| CN103420918B (zh) * | 2013-07-22 | 2015-04-22 | 新发药业有限公司 | 维生素b1关键中间体2-甲基-4-氨基-5-氨基甲基嘧啶的简便制备方法 |
| CN103435556B (zh) * | 2013-08-26 | 2014-11-26 | 新发药业有限公司 | 维生素b1中间体2-甲基-4-氨基-5-氨基甲基嘧啶的合成方法 |
| CN104140420A (zh) * | 2014-07-11 | 2014-11-12 | 江苏兄弟维生素有限公司 | 硫代硫胺的合成工艺 |
| CN104910142A (zh) * | 2015-04-20 | 2015-09-16 | 江苏兄弟维生素有限公司 | 一种制备维生素b1中间体的方法(嘧啶) |
| CN109503426B (zh) * | 2018-12-24 | 2021-11-16 | 江苏兄弟维生素有限公司 | α-(邻氯苯胺基)次甲基-β-甲酰胺基丙腈提纯方法 |
| CN109369540B (zh) * | 2018-12-26 | 2020-09-01 | 浙江本立科技股份有限公司 | 2-甲基-4-氨基-5-甲酰氨甲基嘧啶的合成方法 |
| CN110452181B (zh) * | 2019-08-30 | 2021-01-08 | 厦门金达威维生素有限公司 | 2-甲基-4-氨基-5-甲酰胺甲基嘧啶的合成方法 |
| CN111253320B (zh) * | 2020-03-11 | 2021-05-04 | 山东新和成精化科技有限公司 | 一种甲酰嘧啶的合成方法 |
| CN114230488A (zh) * | 2021-12-27 | 2022-03-25 | 江苏兄弟维生素有限公司 | α–(邻氯苯胺)基次甲基–β–甲酰氨基丙腈的制备方法及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5518702B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-05-12 | 1980-05-21 | ||
| 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 |
-
1984
- 1984-08-25 DE DE19843431270 patent/DE3431270A1/de not_active Withdrawn
-
1985
- 1985-08-12 DE DE8585110089T patent/DE3560169D1/de not_active Expired
- 1985-08-12 EP EP85110089A patent/EP0172515B1/de not_active Expired
- 1985-08-15 US US06/765,505 patent/US4716243A/en not_active Expired - Lifetime
- 1985-08-19 JP JP60180607A patent/JPS6165856A/ja active Granted
- 1985-08-23 HU HU853211A patent/HU195183B/hu not_active IP Right Cessation
- 1985-08-23 DK DK382785A patent/DK382785A/da not_active Application Discontinuation
- 1985-08-23 HU HU873509A patent/HU195785B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0560457B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-09-02 |
| JPS6165856A (ja) | 1986-04-04 |
| US4716243A (en) | 1987-12-29 |
| EP0172515B1 (de) | 1987-05-13 |
| DE3431270A1 (de) | 1986-03-06 |
| DK382785A (da) | 1986-02-26 |
| EP0172515A1 (de) | 1986-02-26 |
| HUT38916A (en) | 1986-07-28 |
| HU195785B (en) | 1988-07-28 |
| DK382785D0 (da) | 1985-08-23 |
| DE3560169D1 (en) | 1987-06-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |