Chlorosuccinimide → 4-(4-Chloromethyl-5-methyl-1,3-thiazol-2-yl)morpholine

Participants

Reaction Steps

To a solution of 4-(4,5-dimethyl-1,3-thiazol-2-yl)morpholine (5.0 g) in acetonitrile (100 mL) was added N-chlorosuccinimide (3.36 g) at room temperature, and the mixture was stirred at the same temperature for 1 hr. 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-(4-chloromethyl-5-methyl-1,3-thiazol-2-yl)morpholine as colorless crystals (2.06 g, 35%) from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 110-111° C.

Provenance & Evidence