Synthesis of some new methyl N-acetyl-aminobenzene disulphonanilides, disulphonic esters and benzo-thiadiazine1, 1-dioxides

ABSTRACT

The diuretic activity of representative benzene disulphonamides has been reported previously. The use of disulphonamides as insecticides and as antibacterial or antifungal has been known. Taylor reported the use of sulphonates as bacteriostatic and fungistatic agents. The aim of this investigation is to procure N-methyl or N-acetylamino disulphonamides and disulphonates derived from o-, m- and p-methylamino-benzene derivatives in the hope of obtaining new derivatives which might posses antibacterial or antifungal activity. Acetylation of methylamino benzene disulphonanilides [I] with one equivalent of acetic anhydride yielded the corresponding monoacetyl derivatives [II] in which the amino group was only acetylated. The structure of these acetylated derivatives [II] was established by elemental analyses, IR spectra and by means of a negative colour test for diazotizable amine. These products [II] also obtained by direct interaction of o-, m- and p-methyl-acetanilidedisulphonyl chlorides with the requisite amine in ether pyridine medium [m.p. and mixed m.p.]