Chloroacetic anhydride → HCID 54105747, compound

Participants

Reaction Steps

34.5 g (122 mmol) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime were stirred with 23 g (140 mmol) of chloroacetic anhydride in 200 ml of N,N-dimethylformamide at room temperature overnight and at 110° for 2 hours. After evaporating the reaction mixture the residue was dissolved in methylene chloride and the solution was washed with saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel while eluting with methylene chloride/methanol 19/1. There were obtained 24 g (58%) of (S)-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-9-one of m.p. 205°-207°.

Provenance & Evidence