ClCCl.C(N(CC)CC)C.[NH2:11][C:12]1[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=1[CH2:14][C:15]1[NH:16][CH:17]=[CH:18][N:19]=1.[C:24](Cl)(Cl)=[S:25]>C(Cl)(Cl)(Cl)Cl>[N:19]1[CH:18]=[CH:17][N:16]2[C:15]=1[CH2:14][C:13]1[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=1[NH:11][C:24]2=[S:25]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°.
Loading…
