WO1998028285A1 - Verfahren zur herstellung von 2-chlor-5-aminomethylthiazol ausgehend von 2-chlor-5-methylthiazol über 2-chlor-5-chlormethylthiazol - Google Patents
Verfahren zur herstellung von 2-chlor-5-aminomethylthiazol ausgehend von 2-chlor-5-methylthiazol über 2-chlor-5-chlormethylthiazol Download PDFInfo
- Publication number
- WO1998028285A1 WO1998028285A1 PCT/EP1997/006843 EP9706843W WO9828285A1 WO 1998028285 A1 WO1998028285 A1 WO 1998028285A1 EP 9706843 W EP9706843 W EP 9706843W WO 9828285 A1 WO9828285 A1 WO 9828285A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- chloro
- aminomethylthiazole
- methylthiazole
- radical
- chloromethylthiazole
- Prior art date
Links
- 0 *c([s]1)cnc1Cl Chemical compound *c([s]1)cnc1Cl 0.000 description 1
- RTEUDRWHKUPKJB-UHFFFAOYSA-N Cc([s]1)cnc1Cl Chemical compound Cc([s]1)cnc1Cl RTEUDRWHKUPKJB-UHFFFAOYSA-N 0.000 description 1
- VRMUIVKEHJSADG-UHFFFAOYSA-N ClCc([s]1)cnc1Cl Chemical compound ClCc([s]1)cnc1Cl VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Definitions
- the present invention relates to a process for the preparation of 2-chloro-5-aminomethylthiazole.
- a process for the preparation of 2-chloro-5-aminomethylthiazole was found, which is characterized in that in a first stage 2-chloro-5-methylthiazole with a radical chlorinating agent in the presence of a radical generator and in the presence of a radical halogenating agent Diluent halogenated up to a conversion of 40 to 70 wt .-% and then added to the resulting reaction mixture with ammonia or aqueous ammonia solution in a second stage and the 2-chloro-5-aminomethylthiazole isolated in a conventional manner.
- the reaction can be represented by the following formula:
- Radical chlorinating agents are preferably N-chlorosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin and trichloroisocyanuric acid.
- the chlorinating agents are used in an amount of 0.5 to 1.3 equivalents of chlorine, based on the thiazole. The approximately equivalent amount of chlorinating agent is preferred.
- the radical generator is used in an amount of 0.01 to 1 equivalent, based on the chlorinating agent. An amount of 0.001 to 0.1 equivalent is preferred.
- diluents which are stable against free radical halogenation: halogenated aromatic or aliphatic hydrocarbons such as e.g. Chlorobenzene, carbon tetrachloride, 1,2-dichloroethane, decachlorobutane and nitrobenzene or acetonitrile.
- halogenated aromatic or aliphatic hydrocarbons such as e.g. Chlorobenzene, carbon tetrachloride, 1,2-dichloroethane, decachlorobutane and nitrobenzene or acetonitrile.
- the reaction is carried out at elevated temperature, preferably from room temperature to 150 ° C., particularly preferably at the boiling point of the diluent.
- the reaction is carried out at normal pressure. But you can also with increased
- the halogenation reaction is carried out until a yield of 2-chloro-5-chloromethylthiazole of 40 to 70% by weight, preferably 50 to 60% by weight, is reached. The reaction is then stopped and the second stage of the reaction is initiated.
- the crude product can also be mixed with aqueous concentrated ammonia solution. It is also possible to add ammonia or ammonia solution to the reaction mixture from the halogenation without first removing the solvent.
- the reaction with ammonia takes place at temperatures from -40 ° C to 150 ° C. You can work at normal pressure but also at elevated pressure. If you work with liquid ammonia, the reaction is preferably carried out in an autoclave at the vapor pressure of the ammonia.
- Example 1 The crude mixture obtained in Example 1 is liquid in an autoclave with 10 ml
- Example 2 The crude mixture obtained in Example 2 is reacted in an autoclave with 30 ml of 65% NH 3 at 70 ° C. and a pressure of 30 bar for 1.5 hours. The mixture was cooled and let down. After degassing in vacuo with aqueous
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR9713589-5A BR9713589A (pt) | 1996-12-20 | 1997-12-08 | Processo para preparação de 2-cloro-5-aminometiltiazol partindo de 2-cloro-5-metiltiazol e passando por 2-cloro-5-clorometiltiazol |
EP97953756A EP0946530A1 (de) | 1996-12-20 | 1997-12-08 | Verfahren zur herstellung von 2-chlor-5-aminomethylthiazol ausgehend von 2-chlor-5-methylthiazol über 2-chlor-5-chlormethylthiazol |
AU57549/98A AU5754998A (en) | 1996-12-20 | 1997-12-08 | Method for producing 2-chloro-5-aminomethylthiazole from 2-chloro-5-methylthiazole via 2-chloro-5-chloromethylthiazole |
JP52829998A JP2001506659A (ja) | 1996-12-20 | 1997-12-08 | 2−クロロ−5−アミノメチルチアゾールの製造方法 |
IL13009297A IL130092A0 (en) | 1996-12-20 | 1997-12-08 | Method for producing 2-chloro-5-aminomethylthiazole from 2-chloro-5-methylthiazole via 2-chloro-5-chloromethylthiazole |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19653586A DE19653586A1 (de) | 1996-12-20 | 1996-12-20 | Verfahren zur Herstellung von 2-Chlor-5-aminomethylthiazol |
DE19653586.7 | 1996-12-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998028285A1 true WO1998028285A1 (de) | 1998-07-02 |
Family
ID=7815722
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1997/006843 WO1998028285A1 (de) | 1996-12-20 | 1997-12-08 | Verfahren zur herstellung von 2-chlor-5-aminomethylthiazol ausgehend von 2-chlor-5-methylthiazol über 2-chlor-5-chlormethylthiazol |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0946530A1 (pt) |
JP (1) | JP2001506659A (pt) |
KR (1) | KR20000069058A (pt) |
AU (1) | AU5754998A (pt) |
BR (1) | BR9713589A (pt) |
DE (1) | DE19653586A1 (pt) |
IL (1) | IL130092A0 (pt) |
WO (1) | WO1998028285A1 (pt) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011118832A1 (ja) * | 2010-03-24 | 2011-09-29 | 住友化学株式会社 | 5-(アミノメチル)-2-クロロチアゾールの製造方法 |
CN114014821A (zh) * | 2021-11-22 | 2022-02-08 | 江苏中旗科技股份有限公司 | 一种噻虫胺的制备方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19908447A1 (de) | 1999-02-26 | 2000-08-31 | Bayer Ag | Verfahren zur Herstellung von 2-Chlor-5-chlormethylthiazol |
DE10061083A1 (de) | 2000-12-08 | 2002-06-13 | Bayer Ag | Bis-(2-chlor-thiazolyl-5-methyl)-amin und seine Salze sowie Verfahren zur Aufarbeitung von 5-Aminomethyl-2-chlor-thiazol und Bis-(2-chlor-thiazol-5-methyl)-amin enthaltenden Reaktionsgemischen |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1067097A (en) * | 1961-06-16 | 1967-05-03 | Merck & Co Inc | Chloroalkyl thiazoles |
EP0391205A1 (de) * | 1989-04-07 | 1990-10-10 | Bayer Ag | Verfahren zur Herstellung von 2-Chlor-5-aminomethylpyridin |
EP0446913A1 (en) * | 1990-03-16 | 1991-09-18 | Takeda Chemical Industries, Ltd. | Process for the preparation of chlorothiazole derivatives |
JPH03223252A (ja) * | 1989-12-27 | 1991-10-02 | Nippon Soda Co Ltd | 置換メチルアミン類の製造方法 |
JPH05286936A (ja) * | 1992-04-06 | 1993-11-02 | Takeda Chem Ind Ltd | ホルムアミド誘導体の製造法及び新規ホルムアミド誘導体 |
EP0775700A1 (en) * | 1995-11-22 | 1997-05-28 | Kureha Chemical Industry Co., Ltd. | Process for the replacement of a primary amino group by a chlorine atom and utilization of this process for the preparation of 2-chloro-5-chloromethyl-thiazol |
WO1997023469A1 (en) * | 1995-12-21 | 1997-07-03 | Novartis Ag | Process for the preparation of 2-chloro-5-chloromethyl-thiazole |
-
1996
- 1996-12-20 DE DE19653586A patent/DE19653586A1/de not_active Withdrawn
-
1997
- 1997-12-08 JP JP52829998A patent/JP2001506659A/ja active Pending
- 1997-12-08 BR BR9713589-5A patent/BR9713589A/pt not_active Application Discontinuation
- 1997-12-08 EP EP97953756A patent/EP0946530A1/de not_active Withdrawn
- 1997-12-08 KR KR1019997004473A patent/KR20000069058A/ko not_active Application Discontinuation
- 1997-12-08 WO PCT/EP1997/006843 patent/WO1998028285A1/de not_active Application Discontinuation
- 1997-12-08 AU AU57549/98A patent/AU5754998A/en not_active Abandoned
- 1997-12-08 IL IL13009297A patent/IL130092A0/xx unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1067097A (en) * | 1961-06-16 | 1967-05-03 | Merck & Co Inc | Chloroalkyl thiazoles |
EP0391205A1 (de) * | 1989-04-07 | 1990-10-10 | Bayer Ag | Verfahren zur Herstellung von 2-Chlor-5-aminomethylpyridin |
JPH03223252A (ja) * | 1989-12-27 | 1991-10-02 | Nippon Soda Co Ltd | 置換メチルアミン類の製造方法 |
EP0446913A1 (en) * | 1990-03-16 | 1991-09-18 | Takeda Chemical Industries, Ltd. | Process for the preparation of chlorothiazole derivatives |
JPH05286936A (ja) * | 1992-04-06 | 1993-11-02 | Takeda Chem Ind Ltd | ホルムアミド誘導体の製造法及び新規ホルムアミド誘導体 |
EP0775700A1 (en) * | 1995-11-22 | 1997-05-28 | Kureha Chemical Industry Co., Ltd. | Process for the replacement of a primary amino group by a chlorine atom and utilization of this process for the preparation of 2-chloro-5-chloromethyl-thiazol |
WO1997023469A1 (en) * | 1995-12-21 | 1997-07-03 | Novartis Ag | Process for the preparation of 2-chloro-5-chloromethyl-thiazole |
Non-Patent Citations (2)
Title |
---|
CHEMICAL ABSTRACTS, vol. 116, no. 7, 17 February 1992, Columbus, Ohio, US; abstract no. 59366r, KAKU S. ET AL.: "Preparation of chlorine-containing heterocyclic group-substituted methylamines" page 862; column 2; XP002063442 * |
CHEMICAL ABSTRACTS, vol. 120, no. 15, 11 April 1994, Columbus, Ohio, US; abstract no. 191511w, UNEME H. & MINAMIDA I.: "Heterocycle-substituted formamide derivatives and their preparation" page 1027; column 2; XP002063443 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011118832A1 (ja) * | 2010-03-24 | 2011-09-29 | 住友化学株式会社 | 5-(アミノメチル)-2-クロロチアゾールの製造方法 |
CN114014821A (zh) * | 2021-11-22 | 2022-02-08 | 江苏中旗科技股份有限公司 | 一种噻虫胺的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
BR9713589A (pt) | 2000-04-04 |
AU5754998A (en) | 1998-07-17 |
DE19653586A1 (de) | 1998-06-25 |
IL130092A0 (en) | 2000-02-29 |
KR20000069058A (ko) | 2000-11-25 |
EP0946530A1 (de) | 1999-10-06 |
JP2001506659A (ja) | 2001-05-22 |
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