Trichloromethanethiol → 5-Chloro-3-(phenoxymethyl)-1,2,4-thiadiazole

Participants

Reaction Steps

To a solution of 2-phenoxyethanimidamide hydrochloride (2.00 g, 10.7 mmol) and perchloromethyl mercaptan (1.15 ml, 10.7 mmol) in dichloromethane (40 ml) was added dropwise a solution of sodium hydroxide (2.15 g, 53.7 mmol) in water (6 ml) under ice-cooling. Then, the reaction mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The organic layer was separated, washed with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=9:1) to give 1.66 g (68.3%) of the desired product as an oil.

Provenance & Evidence