Chloroacetic anhydride → HCID 22914351, compound

Participants

Reaction Steps

A suspension of 5.8 g (0.020 mol) of 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime in 60 ml of dimethylformamide was treated with 3.9 g (0.023 mol) of chloroacetic anhydride. The yellow solution obtained was stirred at 100° for 11/2 hr. and then completely freed from solvents. The oily product crystallized from acetonitrile and was filtered off. The mother liquor was concentrated, the residue was chromatographed over silica gel with dichloromethane/methanol 97:3 as the eluent and the additional portion of product obtained was recrystallized from acetonitrile. There were obtained a total of 4.05 g (59%) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals; m.p. 245°-247°.

Provenance & Evidence