Thionyl Chloride → 5-(chloromethyl)-1-methyl-1H-imidazole hydrochloride

Participants

Reaction Conditions

Reaction Steps

A mixture of (1-methyl-1H-imidazol-5-yl)methanol (500 mg, 4.5 mmol) in DMF (5 mL) at −5° C. was slowly treated with thionyl chloride (0.49 mL, 6.7 mmol), stirred an additional 10 minutes at −5° C., warmed to room temperature, stirred 1.5 hours, cooled to −5° C., quenched with isopropyl alcohol and ethyl acetate, stirred 30 minutes at −5° C., concentrated under vacuum, and filtered to collect the solid. The solid was rinsed with ethyl acetate and dried under vacuum to give (212 mg, 28%) of the desired product as the hydrochloride salt. MS (DCI) m/e 131 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 9.10 (s, 1H), 7.76 (s, 1H), 5.02 (s, 2H), 3.88 (s, 3H).

Provenance & Evidence