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

HRID 331188

Reaction equation

HRID 331188 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-906813f66a2b49e89bf0d203116b5627
Source dataset
uspto-grants-2014_11
Patent number
US08877757B2

Linked notes

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