Chloroacetone → 1-(2-Phenyl-1,3-thiazol-5-yl)ethan-1-one

Participants

Reaction Steps

A mixture of 10.0 g (72.9 mmol) of thiobenzamide and 17.4 g (146 mmol) dimethylformamide dimethyl acetal was stirred at room temperature for 2 hours. The volatiles were evaporated under reduced pressure. The residue was dissolved in ethanol (40 ml). To this solution was added 1.0 g (109 mmol) of chloroacetone and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was diluted with ethyl acetate and washed twice with aqueous sodium bicarbonate, once with water, once with brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using 3:97 acetone:hexanes as eluant to give 3.5 g of the title compound (25%). 1H NMR (500 MHz, CDCl3) δ 8.36 (s, 1H), 8.01 (d, 2H), 7.49 (m, 3H), 2.61 (s, 1H).

Provenance & Evidence