Dichloromethane → 11H-imidazo[1,2-c][1,3]benzodiazepine-5(6H)-thione

Participants

Reaction Steps

Dichloromethane (42,000 ml) and 5,120 g (50.65 moles) of triethylamine were charged into a 20 gallon flask. The solution was stirred under nitrogen atmosphere and 4,370 g (25.23 moles) of 2-(2-aminobenzyl)imidazole were added. The suspension was cooled to 0°-5° and 3,421 g (29.75 moles) of 85% thiophosgene in carbon tetrachloride were added over 3 hours, during which time the reaction temperature rose slowly to 15°. The suspension was then stirred at 10° for 4 hours and at ambient temperature overnight. The precipitated product was collected, washed with 2×3000 ml of dichloromethane and 5×4000 ml of water, and dried (5 mm Hg/60°) to give 11H-imidazo[1,2-c][1,3]benzodiazepine-5(6H)-thione, m.p. 182°-183°.

Provenance & Evidence