Synthesis
Cooled 4-aminoacetophenone (10 mmol) was dissolved in pyridine (10 mL) at 0 °C and methanesulfonyl chloride (15 mmol) was added slowly. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was diluted with H2O and extracted with ethyl acetate (EtOAc) several times. The organic layers were combined, washed sequentially with H2O and saturated brine and dried over anhydrous magnesium sulfate (MgSO4). After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by rapid column chromatography on silica gel, the eluent being a mixed solvent of ethyl acetate:hexane to afford N-(4-acetylphenyl)methanesulfonamide (Compound 13-5, LJO-298). The yield was 95% and the melting point was 161 °C. 1H NMR (CDCl3) δ: 7.97 (dd, 2H, J = 2.0, 6.8 Hz), 7.26 (dd, 2H, J = 2.0, 6.8 Hz), 6.87 (bs, 1H), 3.10 (s, 3H), 2.59 (s, 3H).
References
[1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 6, p. 846 - 867
[2] Organic Process Research and Development, 1998, vol. 2, # 2, p. 71 - 77
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 18, p. 6043 - 6053
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2685 - 2688
[5] Patent: WO2005/3084, 2005, A1. Location in patent: Page 79
