C(N(CC)CC)C.[CH3:8][N:9]1[C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[CH:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:12][CH2:11][C:10]1=[O:27].Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(Cl)(Cl)Cl>[CH3:8][N:9]1[C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[CH:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:12]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:11][C:10]1=[O:27]2.8 ml. (0.02 moles) of triethylamine are added to a solution of 5.73 g. (0.02 moles) of 1-methyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 30 ml. of chloroform, and a solution of 2 ml. of ethyl chloroformate in 10 ml. of chloroform is added to the stirred mixture at room temperature. After 3 hours of stirring 1.4 ml. (0.01 moles) of triethylamine and a solution of 1 ml. of ethyl chloroformate in 5 ml. of chloroform are added to the reaction mixture. The reaction mixture is stirred for an additional 2 hours and then evaporated to dryness under reduced pressure. The residue is crystallized from ethanol. 6.7 g. (92.5%) of crystalline 1-methyl-4-ethoxycarbonyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are obtained; m.p.: 173°-174° C., Rf1 = 0.5.
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