Potassium Carbonate → (2Z)-2-acetyloxyimino-2-(5-chloro-2-formamido-1,3-thiazol-4-yl)acetic acid

Participants

Reaction Steps

To a suspension of 2-(2-formylaminothiazol-4-yl)-2-(Z)-(acetoxyimino)acetic acid (5 g) in tetrahydrofuran (50 ml) was added N-chlorosuccinimide (3.89 g) at room temperature. After the mixture was stirred at room temperature for 5 hours 28 minutes, the reaction mixture was poured into a mixture of 5% aqueous sodium thiosulfate solution (25 ml) and ethyl acetate (50 ml) under ice-cooling. The mixture was adjusted to pH 3.0 with 30% aqueous potassium carbonate solution under ice-cooling, stirred for 1 hour at the same temperature, and the resulting precipitate was collected by filtration to give 2-(5-chloro-2-formylaminothiazol-4-yl)-2-(Z)-(acetoxyimino)-acetic acid (4.02 g).

Provenance & Evidence