Pyridine → HCID 3860452, compound

Participants

Reaction Steps

2-Bromobenzenesulfonyl chloride [(X), 5.9 g, 23.5 mmol] was added dropwise to a stirred 0° C. suspension of 2-bromobenzylamine hydrochloride [(II), R=(4-bromophenyl)methyl, 4.79 g, 19.6 mmol], pyridine (7.9 mL, 97.9 mmol) and 4-dimethylaminopyridine (0.23 g, 1.96 mmol) in dichloromethane (10 mL). The reaction mixture was then stirred at room temperature for 1 hour, then triethylamine (2.73 mL, 19.6 mmol) was then added at 0° C. After stirring overnight at room temperature, the reaction was diluted with dichloromethane (100 mL) then washed with water (50 mL), 0.5N HCl (2×50 mL), water (50 mL), saturated aq. NaHCO3 (2×50 mL) and water (50 mL). The dichloromethane solution was dried (brine, MgSO4) and silica gel (80 mL) was added. The solution was concentrated and the adsorbate was flash chromatographed (4:1 petroleum ether:ethyl acetate) to provide the title compound as a white solid (5.92 g, 75%): mp 108°-110° C.; NMR (CDCl3, 300 MHz): d 8.08 (m, 1H, ArH), 7.70 (m, 1H, ArH), 7.55-7.30 (m, 4H, ArH), 7.08 (d, 2H, ArH), 5.42 (t, 1H, NH), 4.07 (d, 2H, CH2); Anal. (C13H11Br2NO2S) C, H, N.

Provenance & Evidence