Synthesis
4-Bromobenzenesulfonyl chloride (1.00 g, 3.91 mmol) was dissolved in dichloromethane (30.00 mL) and cooled in an ice bath. Diethylamine (1.19 mL, 11.54 mmol) was added slowly and dropwise to the reaction mixture, stirred for 5 minutes, then removed from the ice bath and stirring was continued for 12 hours at room temperature. After completion of the reaction, the reaction solution was concentrated under reduced pressure and the resulting residue was dissolved in dichloromethane and washed sequentially with water and saturated saline. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3:1) to afford the target compound 4-bromo-N,N-diethylbenzenesulfonamide (1.10 g, 96% yield).1H NMR (CDCl3, 500 MHz) δ 7.67 (4H, m), 3.23 (4H, q, J = 7.0 Hz), 1.13 (6H, t).
References
[1] Patent: EP3327000, 2018, A1. Location in patent: Paragraph 0102
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 21, p. 3878 - 3894
[3] Journal of the American Chemical Society, 1923, vol. 45, p. 2697
[4] Journal of Organic Chemistry, 2003, vol. 68, # 21, p. 8274 - 8276
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6575 - 6577
