[C-]#[N:2].[Na+].N.[C:5]1([C:11]2[C:17]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=3[N:15]3[C:23]([CH:26]=[O:27])=[N:24][N:25]=[C:14]3[CH2:13][N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(Cl)Cl>C(O)(C)C.[O-2].[O-2].[Mn+4]>[C:5]1([C:11]2[C:17]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=3[N:15]3[C:23]([C:26]([NH2:2])=[O:27])=[N:24][N:25]=[C:14]3[CH2:13][N:12]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=10.245 g (0.005 mole) of sodium cyanide is added at 0°, with stirring, to the saturated solution of ammonia in 15 ml of isopropanol. After 5 minutes, a solution of 0.322 g (0.001 mole) of 6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carboxaldehyde in ca. 10 ml of isopropanol is added together with 0.87 g of manganese dioxide. After a further 10 minutes, another addition is made of 0.87 g (total 0.02 mole) of manganese dioxide, and the mixture stirred for 4 hours at 0°. After the addition of ca. 40 ml of methylene chloride, the reaction mixture is filtered and the filtrate concentrated by evaporation. Crystallisation of the residue from methanol/ethyl acetate/petroleum ether yields 6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4] benzodiazepine-1-carboxamide, M.P. 285°-289°.
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