SYNTHESIS OF TWO NEW N-BENZAMIDOMETHYL DERIVATIVES OF TOLUENESULFONAMIDE BY DIFFERENT SYNTHETIC ROUTES

Abstract

Sulfonamide compounds are among the first drugs that paved the way for the antibiotic revolution in medicine. The chemical part of sulfonamides is also present in other drugs that are not antibiotics, including thiazide diuretics, anti-diabetic drugs, COX-2 inhibitors, etc.

In order to prepare new derivatives of sulfa drugs, various synthetic procedures were performed to obtain different benzamidomethyl derivatives of toluenesulfonamide.

In two different synthetic procedures, N-benzamidomethyl-N-phenyl-4-toluenesulfonamide was obtained with a high yield, while in the first procedure, reactions of 4-toluenesulfonyl chloride with (benzamidomethyl)phenylamine were performed, and in the second procedure, reactions of N-phenyl-4-toluenesulfonamide with (benzamidomethyl)triethylammonium chloride were performed while N-benzamidomethyl-N-methyl-4-toluenesulfonamide was also obtained in high yield in reactions of 4-toluenesulfonyl chloride with (benzamidomethyl)methyl amine and the other reaction between N-methyl-4-toluenesulfonamide with (benzamidomethyl)triethylammonium chloride.

The structures of the new compounds were confirmed and characterized by IR,  ¹H –NMR, ¹³C –NMR, UV spectroscopic methods and mass spectrometry.