The synthesis of some p-substituted benzenesulfonyl guanidines

In view of the structural similarity of urea and guanidine combined with the fact that certain derivatives of sulfonylurea have been found to be active as oral hypogycemic agents, it seemed desirable to prepare several p-substituted benzenesulfonyl guanidines for further testing as hypoglycemic agents. The synthesis of p-cyanobenzenesulfonyl cyclohexylguanidine was performed by direct condensation of equal molar quanities of p-cyanobenzenesulfonyl chloride with cyclohexylguanidine hydrochloride in an aqueous-acetone solution. Also p-cyanobenzenesulfonyl n-butylguanidine was synthesized by the same procedure. The imino-ester hydrochloride was prepared from p-cyanobenzenesulfonyl cyclohexylguanidine by saturating a solution of the nitrile in ether and absolute ethanol at room temperature with dry hydrogen chloride. The p-N-n-propyl carbamidino was then prepared from the iminoester hydrochloride; i.e., N' - [(p-carbethoxyimino) benzenesulfonyl] cyclohexylguanidine hydrochloride.