3-SULFAMOYL-BENZOICACID

White solid

To ice-cold solution of ammonium hydroxide (25percent, 250ml) is added 3-(chlorosulfonyl) benzoic acid (25g, commercially available, Aldrich) portionwise and the mixture is stirred at room temperature for 15h. The solvent is removed under vacuum to about 50ml and the mixture is acidified with cone. HCl. The precipitate is collected by filtration and dried under vacuum to afford 22g (96percent) of the title compound as a white solid. IH NMR (DMSO-d6) δ 13.44 (br s, IH), 8.38 (s, IH), 8.14 (d, J = 7.5 Hz, IH), 8.04 (d, J = 7.9 Hz, IH), 7.72 (t, J = 7.9 Hz, IH), 7.49 (s, 2H), HPLC (max plot) 97percent; Rt 0.68 min. LC/MS: (ES-): 199.8.To 75 mL of 0 °C cold ammonia (25percent in water) (1002 mmol 30.0 eq) 7.4 g of 3-(chlorosulfonyl)benzic acid, S4, (33.54 mmol, 1.0 eq) was added portion wise. The mixture was stirred for 2 hours at room temperature. The solvent was removed under reduced pressure. The residue was suspended in 25 mL of water and 40 mL of conc. hydrochloric acid were added. The precipitate was collected by vacuum filtration and was washed with water.The crude product was suspended in water and lyophilized to give 6.42 g (95percent) white solid.General procedure: To a saturated solution of 3-chloro sulfonyl benzoic acid (8 mmol) in ethyl acetate (4 mL) was added cold concentrated ammonia or methylamine aqueous solution. After stirring for 30 min at 0 deg C., the mixture was neutralized with a solution of HCl in dioxane (4M) and extracted with ethyl acetate. The organic phase was concentrated under reduced pressure to give a solid which was recrystallized from acetonitrile to give desired compound.   3-Sulfamoyl-benzoic Acid[0234][0235]White solid, yield 64.6percent,

Molecular Weight:201.20
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:201.00957888
Monoisotopic Mass:201.00957888
Topological Polar Surface Area:106
Heavy Atom Count:13
Complexity:292
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes