Sodium hydride → [(4-Chlorophenyl)-(3-methoxy-benzenesulphonyl)-amino]-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-chlorophenyl)-3-methoxy-benzenesulfonamide (900 mg, 3.02 mmol) in anhydrous THF (40 mL) was added sodium hydride (146 mg, 3.62 mmol) at 0-5° C. under nitrogen. The mixture was stirred at 25° C. for 30 minutes. Methyl bromoacetate (463 mg, 3.02 mmol) was then added, stirred for 1 h at 25° C. A further amount of methyl bromoacetate (232 mg, 1.51 mmol) was added, and stirring continued for another 12 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate (3×20 ml). The combined organic layer was washed with water, dried (Na2SO4), evaporated under reduced pressure to yield the title compound as oily compound, which was used as such in the next step. Yield: 1.03 g (92%).

Provenance & Evidence