Chloroacetic anhydride → HCID 53864688, compound

Participants

Reaction Steps

4.4 g (13.8 mmol) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid hydrazide were stirred at room temperature overnight in 30 ml of N,N-dimethylformamide with 2.65 g (15.5 mmol) of chloroacetic anhydride. After evaporating the solvent the residue was stirred at room temperature for 48 hours with 20 ml of a 10% solution of phosphorus pentoxide in methanesulphonic acid. The reaction mixture was treated with ice, made alkaline with conc. sodium hydroxide solution and extracted four times with methylene chloride. By drying the organic phase over magnesium sulfate and evaporating the solvent there were obtained 3.39 g (60%) of (S)-8-chloro-1-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 185°-189°.

Provenance & Evidence