Synthesis of some new sulfonamide derivatives from acetanilide and amino acids and confirmation of their structures by spectroscopic techniques

A convenient, mild, eco-friendly, economical and efficient one-step synthesis of new sulfonamides derived from acetanilide by Hinsberg's reaction between p-acetamido benzene sulfonyl chloride (resulted by chlorosulfonation of acetanilide) and some amino acids (Glycine, Alanine, Phenylalanine, Valine) is described in the presence of sodium carbonate as an acid scavenger and water as a solvent at room temperature. The intermediate compound (of p-acetamido benzene sulfonyl chloride) was initially prepared in a yield of 83.1% by reacting chlorosulfonic acid with acetanilide. Four new sulfonamides were then prepared: the first compound was 2-(4′-acetamidophenyl sulfonamido) Acetic acid in a yield of 89.7% by reaction of the intermediate compound with Glycine, the second compound was 2-(4′-acetamidophenyl sulfonamido)-2-isopropyl Acetic acid in a yield of 93.6% by reaction of the intermediate compound with Alanine, the third compound was 2-(4′-acetamidophenyl sulfonamido) -2-benzyl Acetic acid in a yield of 94.1% by reaction of the intermediate compound with Phenylalanine, finally the fourth compound was 2-(4′-acetamidophenyl sulfonamido)-2-methyl Acetic acid in a yield of 82.6% by reaction of the intermediate compound with Valine. The structures of the new sulfonamides confirmed by spectroscopic analysis techniques: Fourier transform infrared spectroscopy (FT-IR) to identify different types of bonds and functional groups in the unknown compounds, and mass spectrometry with electrospray ionization (ESI-MS) to identify the unknown compounds by determining their molecular weights.