Different derivatives of chalcone-possessing benzimidazole as a prime motif were synthesized by the authors by acid catalyzed aldol condensation reaction. The synthesis of the desired compounds was initiated by undertaking two parallel reactions: (i) synthesis of 2-mercaptobenzimidazole and (ii) synthesis of N-(4-acetylphenyl)-2-chloroacetamide from 4-aminoacetophenone. The two intermediates so prepared were condensed to yield 2-(1H-benzo[d]imidazol-2-ylthio)-N-(4-acetylphenyl)acetamide (II) using acetone as solvent and K2CO3 as a scavenger. The resultant product was further reacted with differently substituted aldehydes to produce the titled compounds using thionyl chloride (SOCl2) in catalytic amount. The synthesized compounds were confirmed for their structure by means of various spectrometric techniques like IR, 1 H NMR, 13C NMR, Mass spectra, and Elemental analysis. Thus-obtained chalcone derivatives were tested for their antibacterial and antifungal activities and were reported in form of minimum inhibitory concentration values.