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

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Thiazole And Isothizaole Compounds (AREA)

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• 1996
  • 1996-12-20 DE DE19653586A patent/DE19653586A1/de not_active Withdrawn
• 1997
  • 1997-12-08 AU AU57549/98A patent/AU5754998A/en not_active Abandoned
  • 1997-12-08 BR BR9713589-5A patent/BR9713589A/pt not_active Application Discontinuation
  • 1997-12-08 JP JP52829998A patent/JP2001506659A/ja active Pending
  • 1997-12-08 IL IL13009297A patent/IL130092A0/xx unknown
  • 1997-12-08 WO PCT/EP1997/006843 patent/WO1998028285A1/de 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

Non-Patent Citations (1)

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