1,3-Dichloroacetone → 4-(Chloromethyl)-2-isopropyl-1,3-thiazole

Participants

Reaction Steps

A mixture of 2-methylpropanethioamide (5.20 g), 1,3-dichloro-2-propanone (7.03 g) and ethanol (100 mL) was heated under reflux for 2 hrs. The reaction mixture was concentrated and ethyl acetate was added to the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 4-chloromethyl-2-isopropyl-1,3-thiazole as a colorless oil (6.33 g, yield 72%) from a fraction eluted with ethyl acetate-hexane (1:20, v/v).

Provenance & Evidence