A series of Schiff base of 4,4'-sulfonyldianiline/ 4,4'-sulfonylbis(2,6- dichlo/dibromo/diiodo dianiline) have been synthesized under microwave ir radiation and conventional heating for comparison. 4,4'-sulfonyldianiline/ 4,4'-sulfonylbi s(2,6- dichlo/ dibromo/ diiodo dianiline) was condensed with hydroxy halo substituted aromatic a ldehyde in ethanol/DMF in the presence of Glacial acetic acid as a catalyst under conventiona l heating and microwave irradiation to yield the Schiff base respectively (2a-p). The microwave assisted reaction was remarkably successful with higher yield within less reaction time compare d to conventional heating method. Spectral data (IR, NMR and Mass spectra) confirmed the struc tures of the synthesized compounds. All the synthesized products are screened for their in vitr o antibacterial activity. The results indicated that the synthesized compounds have moderate to pot ent activities at low and high concentration with reference to their appropriate reference stand ards.