Methanol → 4-{[4-(Methanesulfonyl)benzene-1-sulfonyl]amino}benzoic acid

HRID 1676956Notes

Reaction equation

HRID 1676956 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1.CO.[OH-].[Na+]>O1CCCC1>[CH3:23][S:20]([C:17]1[CH:16]=[CH:15][C:14]([S:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:24])=[O:2])=[CH:5][CH:6]=2)(=[O:13])=[O:12])=[CH:19][CH:18]=1)(=[O:21])=[O:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 46534828Methyl 4-{[4-(methanesulfonyl)benzene-1-sulfonyl]amino}benzoate

Product 1

HCID 253914664-{[4-(Methanesulfonyl)benzene-1-sulfonyl]amino}benzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 4-(4-methanesulfonyl-benzenesulfonylamino)-benzoic acid methyl ester (0.456 g, 1.26 mmol) in a mixture of tetrahydrofuran (10 mL)/methanol (10 mL) is added 2N sodium hydroxide (2 ml, 4.0 mmol) and the reaction is heated to reflux for 1 hour. The reaction is then concentrated to dryness and the residue is dissolved in 95% dichloromethane/5% isopropanol and washed with 0.1N HCl. The organic layer is separated and dried over anhydrous sodium sulfate, filtered, and concentrated to provide 0.403 g (90%) of the pure title compound. MS (ES−) m/e 354.0 (M−1)−.

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 1 hour
  3. concentrationThe reaction is then concentrated to dryness
  4. dissolutionthe residue is dissolved in 95% dichloromethane/5% isopropanol
  5. washwashed with 0.1N HCl
  6. customThe organic layer is separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-94ec8a4697434d43a7f4b4fdd7d1d69b
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

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