Hydrochloric Acid → (4-Sulfamoylphenoxy)acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of NaH (2.8 g, 0.07 mol, 50% in mineral oil) in DMF (50 mL) is added dropwise methyl glycolate (5.5 g, 0.06 mol) over a period of 10 min. The mixture is heated up to 50° C. for 3 h and cooled down to room temperature. 4-Fluorobenzenesulfonamide g, 0.0114 mol) is added portionwise. After stirring at 50° C. for 10 h, the reaction mixture is cooled down and poured into ice-water containing HCl. The product is extracted with DCM (2×100 mL). The combined organic phase is washed with water and dried over Na2SO4. The solvent is evaporated under reduced pressure and the residue is purified by chromatography (silica gel, 60-120 mesh) with chloroform/methanol (9/1) as eluent to afford 900 mg (32%) of the title compound as a solid. 1H NMR (CDCl3, 400 MHz) δ 7.68-721 (m, 2H), 7.10-7.12 (m, 2H), 6.45 (br s, 2H), 4.51 (s, 2H), 3.86 (s, 3H).

Provenance & Evidence