Methanol → Benzoic acid, 3-(aminosulfonyl)-, methyl ester

HRID 655615

Reaction equation

HRID 655615 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].S(Cl)(Cl)=O.[CH3:18]O>>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH3:18])=[O:9])(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2293523-Sulfamoylbenzoic acid

Product 1

HCID 108836Benzoic acid, 3-(aminosulfonyl)-, methyl esterYield 73%

Procedure

To a solution of 3-(aminosulfonyl)benzoic acid (22 g, 0.109 mol) in MeOH (250 ml) is added thionyl chloride (25 ml, 0.328 mol) and the mixture is refluxed for 16 h. The solvent is removed and the residue is diluted with EtOAc (200 ml), washed with a 10% solution of sodium bicarbonate, water and brine. The solvent was removed under vacuum to afford 17 g (73%) of the title compound as a solid. 1H NMR (DMSO-d6) δ 8.39 (t, J=1.5 Hz, 1H), 8.16-8.13 (m, 1H), 8.09-8.05 (m, 1H), 7.76 (t, J=7.9 Hz, 1H), 7.53 (s, 2H), 3.90 (s, 3H). HPLC (max plot) 99%; Rt 1.49 min. LC/MS: (ES+):215.9, (ES−):214.1.

Workup

  1. temperaturethe mixture is refluxed for 16 h
  2. customThe solvent is removed
  3. additionthe residue is diluted with EtOAc (200 ml)
  4. washwashed with a 10% solution of sodium bicarbonate, water and brine
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-36490e8a8c754e9fa56472c859f1d6bd
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Linked notes

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