Methyl chloroacetate → Methyl 4-amino-2-anilino-1,3-thiazole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 0.5 M solution of sodium methoxide in methanol (44.4 mL, 22.19 mmol) was added dropwise to a suspension of isothiocyanato-benzene Compound 3a (2.0 g, 14.79 mmol) and NH2CN (0.684 g, 16.27 mmol) in methanol (50 mL) at 0° C. The mixture was stirred at r.t. until Compound 3a was no longer detected (about 3 hrs). Methyl chloroacetate (1.56 mL, 17.75 mmol) was added at r.t. and the mixture was warmed to 50-60° C. and stirred at 50-60° C. for about 3 hrs, then stirred at r.t. overnight. The mixture was evaporated to dryness in vacuo and the resultant solid was thoroughly washed with water, methylene chloride and a small amount of methanol to give 4-amino-2-phenylamino-thiazole-5-carboxylic acid methyl ester Compound 3b (1.12 g, 60%) as a yellow powder. MS 250 (M+H+), 248 (M−H+)

Provenance & Evidence