2-HYDROXY-5-(4-METHOXY-PHENYLSULFAMOYL)-BENZOIC ACID synthesis

Yield:-

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 16 h;

Steps:

543

A solution of 5-chlrosulfonylsalicylic acid (0.96 g, 4.1 mmol) in dichloromethane (20 ml_) and triethylamine (1 .69 ml_, 12.2 mmol) was added p-anisidine (0.49 g, 4.1 mmol) and the resulting mixture was stirred at room temperature for 16 hours. The mixture was added dichloromethane (50 ml_) and was washed with water (2 x 100 ml_). Drying (MgSO₄) of the organic phase and concentration in vacuo afforded 0.57 g crude product. Purification by column chromatography on silica gel eluting first with ethyl acetate: heptane (1 :1 ) then with methanol afforded 0.1 g of the title compound.HPLC-MS (Method A): m/z: 346 (M+23); Rt = 2.89 min. EPO ¹H-NMR (DMSO-rf₆): δ 3.67 (3H, s), 6.62 (1 H, d), 6.77 (2H, d), 6.96 (2H, d), 7.40 (1 H, dd), 8.05 (1 H₁ d), 9.6 (1 H₁ bs).

References:

WO2006/82245,2006,A1 Location in patent:Page/Page column 248-249