Water → 2-Chloro-N-[4-(N,2-dimethoxy-2-oxoethanimidoyl)-1,3-thiazol-2-yl]ethanimidic acid

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Reaction Steps

In 90 ml of N,N-dimethylacetamide is dissolved 21.5 g of methyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate (syn-isomer) and, under ice-cooling, 13.6 g of chloroacetyl chloride is added dropwise. The mixture is stirred under ice-cooling for 30 minutes and, then, at room temperature for 30 minutes, after which 500 ml of water is added. The mixture is extracted twice with ethyl acetate and the combined extract is washed with a 5% aqueous solution of sodium hydrogen carbonate and water in that order and dried. On removal of the solvent, there is obtained 25 g of methyl 2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetate(syn-isomer) as crystals melting at 130.8° C.

Provenance & Evidence