Synthesis of a series of dialkylsulphamylbenzoic acids

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Sulphamylbenzoic acids contain both benzoic acid and sulphonamide moieties. Synthetically, sulphamylbenzoic acids are made by preparing first p-toluenesulphonyl chloride through sulphonation of toluene, followed by oxidation of the latter to yield the corresponding p-carboxybenzenesulphonyl chloride. In this research the same strategy was followed. The p-carboxybenzenesulphonyl chloride thus formed was reacted with the appropriate dialkyl amine. The by products formed were removed by treating the reaction medium with a weak alkaline substance, such as aqueous bicarbonate solution, then filtering off the precipitated by products. Acidification of the filtrates gave the desired sulphamylbenzoic acids as crystalline solid materials. The following acids were synthesized in this reseach: p-(diethylsulphamyl)benzoic acid (III), p-(di-n-propylsulphamyl)benzoic acid (IV) and p-(di-isobuthylsulphamyl)benzoic acid (V). This methodology can be used for the preparation and synthesis of any other kind of p-(dialkylsulphamyl)benzoic acid.

Probenecid, p-carboxybenzenesulphonyl chloride, p-diethylsulphamylbenzoic acid, p-di-n-propylph.acid