Triethylamine → Methyl 4-amino-3-phenyl-1,2-thiazole-5-carboxylate

Participants

Reaction Steps

Triethylamine (5.39 g, 53.3 mmol) was added dropwise to a stirred solution of (Z)—N-(tosyloxy)benzimidoyl cyanide (Preparation 103B, 8 g, 26.6 mmol) and methyl 2-mercaptoacetate (2.86 mL, 32.0 mmol) in MeOH (70 mL) at room temperature. After stirring at room temperature for 3 h, the reaction was cooled and treated with 100 mL ice/water. The resultant solid was filtered and washed with water. The solid was vacuum dried to yield 6 g brown colored solid. Recrystallization from hexane/ethyl acetate yielded the titled compound (3 g) as a beige colored needles. The compound had an LC/MS M+1=235.2.

Provenance & Evidence