Thionyl Chloride → 2-Chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazole

Participants

Reaction Steps

To dry dimethylformamide (50 ml)solution of 22.5 g (67.9 mmol)of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (Compound I-8)was added 25.0 ml of thionyl chloride, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and to the residue, ethyl acetate was added and extracted. The extract was neutralized with a saturated aqueous sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give 23.7 g of 2-chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazole (28a)(yield about 100%). mp 110-111° C.

Provenance & Evidence