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According to the literature, 2-(3H)-benzoxazolone and its derivatives are compounds having different pharmacological activities more especially analgesic and anti-inflammatory. Its ability for modification at different positions makes it be of great interest in medicinal and pharmaceutical chemistry. Consequently they can be used in the development of new drug candidates that are COX-2 selective with less side effects. In this research we synthesized two compounds, Compound 1 via Mannich reaction, under reflux condition which involves modification of the 3rd position of 2-(3H)-benzoxazolone. Compound 2 through a reaction at room temperature which involves the modification of the 6th position of 6-(2-bromo-acetyl)-2(3H)-benzoxazolone. The synthesized compounds were characterized using FT-IR and 1H-NMR spectroscopy. Their purity was checked using melting point determination and thin layer chromatography.