Bromochloromethane → HCID 10241417, compound

Participants

Reaction Steps

To a solution of 2-methyl-1,3,4-thiadiazole-5-thiol (2.64 g: 20 mMol.) in dimethylformamide (40 ml) is added under ice cooling sodium hydride (880 mg: 60% dispersion in oil: 1.1 equivalents: 22 mMol.) in portions, and the mixture is stirred for 10 minutes. To the resulting solution is added bromochloromethane (40 ml), and the mixture is stirred at the same temperature for another 1 hour and 30 minutes. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and purified by silica gel chromatography (toluene: ethyl acetate=10:1) to give 5-chloromethylthio-2-methyl-1,3,4-thiadiazole (3.3 g) as colorless oil. Yield: 91%.

Provenance & Evidence