Chloroacetic anhydride → (S)-8-chloro-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one

Participants

Reaction Steps

31.7 g (100 mmol) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H, 11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxamidoxime were suspended in 200 ml of N,N-dimethylformamide and treated with 18.8 g (110 mmol) of chloroacetic anhydride. The reaction mixture was heated to 105° for 2 hours and evaporated. By chromatography of the residue on silica gel while eluting with chloroform/methanol 9/1 there were obtained 27.9 g (74%) of (S)-8-chloro-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 211°-212°.

Provenance & Evidence