(4) Dissolve 10.0 g of 3-amino-4-phenoxyanisole in 50 mL of pyridine. Under cooling conditions in an ice bath, 5.59 g of methanesulfonyl chloride was added slowly dropwise for a controlled time of 10 minutes. The reaction mixture was stirred continuously at 20°C to 25°C for 1 hour. Subsequently, the reaction mixture was poured into a mixture consisting of 200 ml of ethyl acetate and 100 ml of water. The organic layer was separated and washed sequentially with three 100-mL portions of 2N hydrochloric acid and saturated aqueous sodium chloride. After separation of the organic layer, it was dried with anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The resulting crude product was recrystallized by isopropanol to give 12.5 g (yield: 91.9%) of N-(5-methoxy-2-phenoxyphenyl)methanesulfonamide with a melting point of 109.5°C to 111°C. IR (KBr, cm-1): 3250, 1610, 1585, 1480, 1320, 1220, 1150. nMR (CDCl3) δ: 2.94 (3H, s), 3.81 (3H, s), 6.36-7.43 (9H, m).
