Sodium Iodide → N-(5-Acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamide

Participants

Reaction Steps

A mixture of N-(5-acetyl-2-hydroxyphenyl)methanesulfonamide (31) (0.30 g, 1.32 mmol), sodium iodide (0.20 g, 1.32 mmol), potassium carbonate (0.91 g, 6.58 mmol), and benzyl bromide (0.39 mL, 3.28 mmol) in acetone (10 mL) was stirred under reflux for 66 h. After removal of solvent by rotary evaporation, the resulting residue was diluted with dichloromethane and insoluble inorganics were vacuum filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by flash silica gel column chromatography eluting with a mixture of ethyl acetate (0-3%) in dichloromethane to give benzyl ether 32 as a yellow solid (0.54 g, 99%): 1H NMR (300 MHz, CDCl3) δ 2.38 (s, 3H), 2.85 (s, 3H), 4.75 (br, 2H), 5.18 (s, 2H), 7.05 (d, 1H), 7.23 (m, 5H), 7.42 (m, 5H), 7.62 (d, 1H), 7.89 (dd, 1H); m/z (ESI) 410 [C23H23NO4S+H]+.

Provenance & Evidence