decolorizing the solution with activated charcoal darco to give 0 214 g of 8 chloro 6 phenyl 4h s triazolo 4 3 a 1 4 benzodiazepine 1 acetonitrile of melting point 199 5 u00b0 200 5 u00b0 c the analytical sample had a melting point of 198 u00b0 c anal calcd for c 18 h 12 cin 5 c 64 77 h 3 63 cl 10 62 n 20 98 found c 64 52 h 3 86 cl 10 51 n 20 95 in the same manner 1 bromomethyl 8 chloro 6 phenyl 4h s triazolo 4 3 a 1 4 benzodiazepine can be condensed with potassium cyanide in dimethylsulfoxide to give 8 chloro 6 phenyl 4h s triazolo 4 3 a 1 4 benzodiazepine 1 acetonitrile 8 chloro 1 chloromethyl 6 phenyl 4h s triazolo 4 3 a 1 4 benzodiazepine 343 mg 0 001 mole was added to solution of diethylamine 1 ml in dry dimethylformamide 5 ml and the mixture was stirred at ambient temperature under nitrogen for 4 hours 30 minutes sodium iodide 50 mg was added and the mixture was stirred at ambient temperature for 17 hours 30 minutes and heated at 100 u00b0 111 u00b0 c for 6 hours it was then poured into ice water and extracted witch chloroform the extract was washed with water dried over anhydrous potassium carbonate and concentrated in vacuo the residue was crystallized from ethyl acetate skellysolve b hexanes to give 0 277 g of 8 chloro.