Carbon Tetrachloride → 5-(2-bromophenyl)-N-phenyl-1,3,4-oxadiazol-2-amine

Participants

Reaction Steps

To a solution of 1-(2-bromobenzoyl)-4-phenylsemicarbazide (330 mg, 0.98 mmol; Reference Compound 5-(1)), triphenylphosphine (390 mg, 1.5 mmol) and triethylamine (0.20 mL, 9.7 mmol) in methylene chloride (30 mL) were added carbon tetrachloride (2.5 mL, 1.4 mmol) and tetrahydrofuran (5 mL) under ice-cooling. The mixture was refluxed for 2 hours and then cooled to room temperature. Ethyl acetate (20 mL) was added thereto and the ethyl acetate solution was washed with a saturated brine solution (20 mL) twice, dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to dryness. The residue was purified with a silica gel column chromatography (hexane/ethyl acetate) to give 260 mg (82%) of the titled compound as a colorless solid.

Provenance & Evidence