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

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chlorothiobenzamide (0.5 g, 2.9 mmol) and 1,3-dichloroacetone (0.4 g, 3.18 mmol) in EtOH-THF (20 mL-10 mL) was heated to 85° C. for 10 h. The reaction mixture was cooled to room temperature and quenched with 10% NaHCO3 solution. The organic product was extracted with EtOAc and the organic layer was washed with H2O and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 3-5% EtOAc in petroleum ether) to afford 4-(chloromethyl)-2-(4-chlorophenyl)thiazole (0.55 g, yield 77%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.91-7.88 (m, 2H), 7.44-7.41 (m, 2H), 7.33 (s, 1H), 4.75 (s, 2H). MS (ESI) m/z: Calculated for C10H7Cl2NS: 242.97. found: 244.0 (M+H)+.

Provenance & Evidence