Water → 4-Cyclohexylthiazol-2-ylcarbamoylcarboxylic Acid

Participants

Reaction Steps

Ethyl 4-cyclohexylthiazol-2-ylcarbamoylcarboxylate (1.41 g., 5 mmole) was combined with 40 ml. of water and 5 ml. of 1 N potassium carbonate (1 equivalent, 2.5 mmole) was heated on a steam bath for 15 minutes. After 10 minutes, tlc (chloroform-1% ethanol) indicated hydrolysis was almost complete. The hot reaction mixture was clarified by filtration, cooled in an ice-water bath and acidified with 10.5 ml. of 1 N hydrochloric acid. Product (1.02 g.) was recovered by filtration. Recrystallization from isopropyl alcohol gave purified 4-cyclohexylthiazol-2-ylcarbamoylcarboxylic acid [625 mg.; m.p. 198.5°-200.5° C. (dec)].

Provenance & Evidence