1,3-dihydro-2H-benzimidazole-2-one ring system represents the core skeleton of a large number of biologically active, structurally intriguing compounds found in a multitude of pharmaceutically important compounds. The development of efficient and practical methods for construction of this important heterocyclic remains as an active area of synthetic research. The present paper describes the synthesis and antibacterial activity of some novel 1,3- dihydro-2H-benzimidazol-2-one analogs 6a -6g (Scheme 1) from commercially available 1,2-phenylenediamine as starting material. The newly synthesized compounds, 6a-6g were screened in-vitro at a concentration of 100 μg/mL for antibacterial activity against two Gram-positive (Staphylococcus aureus and Staphylococcus pyogenes) and two Gram-negative strains (Escherichia coli and Pseudomonas aeruginosa). It was observed that among all the compounds tested, compound 6e, 6f and 6g showed high activity against all the tested bacterial strains.