Synthesis of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophthalates and Their Sulfonylation

Abstract

Dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate and dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate were obtained in the free form for the first time. The products were sulfonylated with p-toluenesulfonyl to obtain previously unknown dialkyl 5-(4-toluenesulfonamido)-2-hydroxy-4,6-dimethylisophthalates. The use of p-acetamidobenzenesulfonyl chloride as the sulfonylating agent in this reaction led to the formation of dialkyl 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethyl isophthalates. The synthesized sulfonamide derivatives are of interest as potentially biologically active compounds. The structure of all the obtained compounds was proved using IR and NMR spectroscopy and mass spectrometry.