Carbon Disulfide → 1-methyl-6-[5-[[3-(trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]-1H-benzimidazole

Participants

Reaction Conditions

Reaction Steps

A solution (5 mL) of 1-methyl-1H-benzimidazole-6-carbohydrazide (0.20 g, 1.05 mmol), triethylamine (0.18 mL, 1.26 mmol) and carbon disulfide (0.16 mL, 2.63 mmol) in ethanol was heated under reflux overnight. The reaction mixture was cooled to 0° C., potassium hydroxide (58.9 mg, 1.05 mmol) and 3-(trifluoromethyl)benzyl chloride were added, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3) to give the title compound (49.9 mg, yield 12%) as colorless crystals.

Provenance & Evidence