The biological potential of N'-substituted-2-(5-(3-chlorophenyl)-1,3,4-Oxadiazol-2-ylthio)acetohydrazide (8a-p) has been evaluated against bacterial strains of Gram-negative and Gram-positive bacteria. The multistep synthesis involved the conversion of 3-chlorobenzoic acid (1) to ethyl 3-chlorobenzoate (2), 3-chlorobenzohydrazide (3), 5-(3-chlorophenyl)-1,3,4-Oxadiazol-2-thiol (4), ethyl 2-(5-(3-chlorophenyl)-1,3,4-Oxadiazol-2-ylthio) acetate (5) and 2-(5-(3-chlorophenyl)-1,3,4-Oxadiazol-2-ylthio)acetohydrazide (6). The last step involved the reaction of 6 and aryl aldehydes, 7a-p, in methanol to synthesize the Schiff bases, 8a-p, with better yields. The structures of all the molecules were corroborated by spectral analysis. The Schiff bases were further evaluated for the antibacterial activity and found to be moderately good inhibitors of bacterial strains of Gram-bacteria.