Trichloromethanethiol → 3-Benzyl-5-chloro-1,2,4-thiadiazole

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-phenyl-acetamidine hydrochloride (1.078 g, 6 mmol) in dichloromethane (10 ml) was added perchloromethyl mercaptan (0.61 ml, 5 mmol) via syringe. The mixture was cooled in an ice-methanol bath to −10° C. and a solution of sodium hydroxide (1.2 g, 30 mmol) in water (3 ml) was added dropwise keeping the temperature below −8° C. After complete addition the mixture was stirred 10 min at 0° C. The reaction mixture was diluted with water and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were dried over Na2SO4, filtered and the solvents were evaporated. The residue was purified by chromatography on silica gel using heptane/ethyl acetate as eluent. The title compound was obtained as an orange liquid (0.779 g, 62%). MS ISP (m/e): 211.0 (100) [(M+H)+].

Provenance & Evidence