Acetyl chloride → 2-((5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methylimidazol-2-yl)methoxy)ethyl acetate

Participants

Reaction Steps

To dry methylene chloride solution (5 ml) of 200 mg (0.5 mmol) of 2-{[5-(3,5-dichlorophenylthio)-4-isopropyl-1 methyl-1H-imidazol-2-yl]methoxy} ethanol (25a), 161 mg (1.60 mmol) of triethylamine was added. Under ice-cooling, 63 mg (0.8 mmol) of acetyl chloride was added, and the mixture was stirred at the same temperature for 15 minutes. To the reaction mixture, a saturated aqueous solution of sodium hydrogen carbonate was added, neutralized, and extracted with methylene chloride. The extract was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:1) to obtain 200 mg of 2-[-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazol-2-ylmethoxy]ethyl acetate (Compound I-60) as oil (yield 90%).

Provenance & Evidence