[CH:1]1[S:2][CH:3]=[C:4]2[C:10]=1[C:9](=[O:11])[NH:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[NH:5]2.C(C(CC)=O)C.N1C=CC=CC=1.[C:28](Cl)([Cl:30])=[O:29]>C1(C)C=CC=CC=1.O>[Cl:30][C:28]([N:5]1[C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=2[NH:8][C:9](=[O:11])[C:10]2=[CH:1][S:2][CH:3]=[C:4]12)=[O:29]
16.2 gm (0.075 mol) of 4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one were admixed with 160 ml of diethylketone and 5.9 gm (0.075 mol) of pyridine at 40° C., and over a period of 20 minutes 75 ml of a 20% solution of phosgene (0.15 mol) in toluene were added thereto. The reaction mixture was stirred for 2 hours at 40° C. and then for 3 hours at 60° C. After cooling to room temperature, the mixture was stirred with 150 ml of water, then filtered, and the organic phase was separated, concentrated by evaporation in vacuo, and the residue was recrystallized from acetonitrile. 4-Chlorocarbonyl-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one, m.p. of 244°-245° C. (decomp.), was obtained with a yield of 50% of theory.
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