A GENERAL METHOD FOR PREPARING 2-ACETAMIDOACETANILIDES HAVING A 2ND FUNCTIONAL GROUP IN 2 POSITION AND AFFORDING AN ACCESS TO 3-ACETAMIDO-1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES

Base-catalyzed elimination of acetic acid from 2-(N-acetoxyacetamido)acetanilides to afford the reactive and unisolated 2-(acetylimino)acetanilides is described. Available nucleophiles add to the unsaturated imine bond to give 2-substituted 2-acetamidoacetanilides. Special cases are discussed, including a reaction of ammonia with an o-benzoyl-2-(N-acetoxyacetamido)acetanilide that leads ultimately to a 3-acetamido-1,4-benzodiazepine. © 1968, American Chemical Society. All rights reserved.