Guanidine and 1-acetamidoguanidine have been isolated from the hydrogenation of nitroguanidine in acetic acid. Large ratios of catalyst to substrate are necessary for the successful hydrogenation of nitroaminoguanidine in this media. Nitroaminoguanidine undergoes acetylation in acetic acid under mild conditions and the l-acetamido-2-nitroguanidine hydrogenates with much greater ease than the parent substance.l-Aeetamido-2-aminoguanidine can be recovered as derivatives from the reduction products if mild conditions are employed; generally, however, this compound undergoes cyclization to 3-methyl-4,5-diamino-l,2,4-triazole under the conditions of recovery from acidic medium. Acetylation or formylation of diaminoguanidine salts also yields similarly substituted triazoles. Evidence is presented to support the structure assigned to these cyclized products. In basic medium benzal l-aeetamido-2-aminoguanidine undergoes ring closure to benzal 3-methyl-5-hydrazino-l, 2,4-triazole.Chicago, Illinois China Lake, Calif.
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