Potassium Carbonate → N-[2-(2-hydroxyethoxy)ethyl]-1-(2-nitrophenyl)methanesulfonamide

참여 물질

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To a stirred solution of 2-(2-aminoethoxy)ethanol (0.557 g), 5.31 mmol) and potassium carbonate (1.17 g, 8.48 mmol) in toluene (50 ml) and water (4 ml) at room temperature, was added 2-nitro-alpha-toluenesulfonyl chloride (1.00 g, 4.24 mmol) in one portion and the reaction was left to stir overnight. The reaction was diluted with ethyl acetate and water. The organic layer was separated before being washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo. The crude material was purified by column chromatography eluting with ethyl acetate:hexane to afford N-[2-(2-hydroxyethoxy)ethyl]-1-(2-nitrophenyl)methanesulfonamide as product (0.155 g, 12%); Rf (ethyl acetate:hexane 2:1) 0.11; δH (400 MHz, CDCl3) 8.02 (1H, d), 7.67 (2H, m), 7.53 (1H, dt), 5.15 (1H, brs), 4.86 (2H, s), 3.71 (2H, s), 3.56 (4H, m), 3.19 (2H, m) and 2.36 (1H, s); LCMS Rt=2.60 min, m/z (APCI) 305 (MH+).

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