Carbon Tetrachloride → HCID 19910784, compound

Participants

Reaction Steps

To a solution of 810 mg of N-(3,5-dichlorophenyl)-N'-(1,1-diethylpropyl)thiourea produced in Example A-7 and 800 mg of triphenylphosphine in 10 ml of dichloromethane were added 380 mg of triethylamine and 590 mg of carbon tetrachloride. The mixture was refluxed for 4 hours and evaporated in vacuo. The residue was stirred with n-hexane and filtered to remove solid matter. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography using n-hexane as a solvent to give 640 mg of N-(3,5-dichlorophenyl)-N'-(1,1-diethylpropyl)carbodiimide as an oil. To a solution of this oil in 5 ml of DMF were added 470 mg of cyanamide and 0.05 ml of diisopropylethylamine. The mixture was stirred at 100° C. for 3 hours, cooled to room temperature and poured into water. The resulting crystals were collected and recrystallized from benzene to give 480 mg of the title compound as colorless needles melting at 178.5°-180.5° C.

Provenance & Evidence