1,4-Benzodiazepin-2-ones are prepared via the reaction of a haloacetamidophenyl ketone with hexamethylenetetramine in the presence of ammonia. The 1,4-benzodiazepin-2-ones so prepared are known compounds useful as muscle relaxant and anti-convulsant agents.
This is a continuation of application Ser. No. 359,814 filed May 14, 1973, which in turn is a continuation-in-part of application Ser. No. 282,217 filed Aug. 21, 1972. Both applications are now abandoned.
This invention relates to an improved process for the preparation of 1,3-dihydro-2H-1,4-benzodiazepin-2-ones and 2,3-dihydro-1H-1,4-benzodiazepines by the condensation of a 2-(2-haloacylamido)-benzophenone or a 2-(2-haloethylamino)-benzophenone, respectively, in the presence of hexamethylenetetramine, a water miscible alcohol containing 5 to 50 volume percent water, and an ammonium salt.
The invention provides compounds of the formula (I): ##STR1## wherein R.sub.1 is an amino or an alkyl group, optionally substituted with one or more groups selected from C.sub.1- C.sub.6 alkyl group; R.sub.2 is H or halogen; R.sub.3 is H, halogen, hydroxyl group, or alkyl group; R.sub.4 is H or halogen; and R.sub.5 is halogen, preferably chlorine; and salts and prodrugs thereof; and a method of using these compounds for the treatment of cancer.
