Chloroacetone → Ethyl 4-methyl-1,3-thiazole-2-carboxylate

Participants

Reaction Steps

Ethyl thiooxamate (3.0 g, 22 mmol) was dissolved in ethanol (30 mL) under argon. Chloroacetone (1.8 mL, 22 mmol) was added and the resultant solution was heated at 80° C. for 16 h. The reaction mixture was concentrated in vacuo, adsorbed onto silica gel, and purified by column chromatography on silica gel eluting with 97:3, then 95:5 hexane:ethyl acetate to afford ethyl 4-methyl-1,3-thiazole-2-carboxylate (850 mg, 22% yield) as an oil. 1H NMR (CDCl3, 300 MHz) 7.20 (s, 1H), 4.48 (q, J=7.1 Hz), 2.56 (s, 3H), 1.47 (s, 3H). MS (EI ionization) 171 (M+).

Provenance & Evidence