Methyl chloroacetate → HCID 87676872, compound

Participants

Reaction Conditions

Reaction Steps

A solution of MeONa in methanol (25% by wt., 2.0 mL, 9.36 mmol) was added dropwise to a suspension of 4-isothiocyanato-benzonitrile Compound 4a (1.0 g, 6.24 mmol) and NH2CN (0.289 g, 6.87 mmol) in methanol (25 mL) at 0° C. The mixture was stirred at r.t. until Compound 4a was no longer detected (about 3 hrs). Methyl chloroacetate (0.657 mL, 7.49 mmol) was added at r.t. and the mixture was stirred at 50-60° C. for 3 hrs, then at r.t. overnight. The mixture was evaporated to dryness in vacuo, then the residual solid was thoroughly washed with water, methylene chloride and a small amount of methanol to give 4-amino-2-(4-cyano-phenylamino)-thiazole-5-carboxylic acid methyl ester Compound 4b (1.06 g, 62%) as a yellow powder. MS 273 (M−H+)

Provenance & Evidence