Chloromalonaldehyde → HCID 46785475, Verbindung

To a solution of 3-(trifluoromethyl)benzenecarbothioamide (1.31 g, 6.37 mmol) in ethanol (15 mL) was added 2-chloropropane-1,3-dial (2.04 g, 19.1 mmol), and the mixture was heated under reflux overnight. The reaction mixture was extracted with ethyl acetate, washed successively with diluted aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give 2-[3-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde (423 mg) as colorless crystals. The present compound was dissolved in ethanol (5 mL), sodium borohydride (91 mg, 2.47 mmol) was added under ice-cooling, and the mixture was stirred at room temperature overnight. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (334 mg, 78%) as a colorless oil.