Production of 2-(2-aminothiazole-4-yl)-2-(syn)- methoxyimino...

Details Production of 2-(2-aminothiazole-4-yl)-2-(syn)- methoxyimino... Production of 2-(2-aminothiazole-4-yl)-2-(syn)- methoxyimino...

C - Chemistry, Metallurgy

07

D

260/310.5

C07D 277/40 (2006.01) C07D 277/20 (2006.01)

Patent

CA 1163272

Abstract of the Disclosure A process for the production of 2-2(2-aminothiazole-4 -yl)-2-(syn)-methoxyimino acetic ester is described and has the following reaction sequence. Image (a) (b) (c) (d) Image (e) (f) (g) First, a 4-chloroacetoacetic ester (a) is oximized with an alkalinitrate (b) under cooling and then the resultant chloro- hydroxyimino ester (c), in solution form, is reacted without isolating with a thiourea solution (d) to produce a 2-(2- aminothiazole-4-yl)-2-(syn)-hydroxyimino acetic ester (e), the reaction temperature does not exceed +40°C. The latter ester is suspended effectively together with a phase transfer catalyst such as TBAHSO4 (f) (tetrabutyl ammonium sulphate) in an organic solvent, is mixed with caustic soda solution and is methylated with dimethyl sulface to give 2-(2- aminothiazole-4-yl)-2-(syn)-methoxyimino acetic ester such that the reaction temperature does not exceed 0°C.

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