Sodium Hydroxide → 4-(Methylsulfonamido)benzoic acid

HRID 1992236Notes

Reaction equation

HRID 1992236 reaction equation
[OH-].[Na+].[CH3:3][S:4]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)(=[O:6])=[O:5]>CO.O>[CH3:3][S:4]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)(=[O:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 669159Methyl 4-methanesulfonamidobenzoate

Product 1

HCID 2506534-(Methylsulfonamido)benzoic acidYield 74.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3.6 g (90 mmol) of NaOH was added to the solution of methyl 4-[(methylsulfonyl)amino]benzoate in 40 mL methanol and 20 mL water and stirred overnight at room temperature. Solvents were then removed and the product purified by ethyl acetate extraction from 1N aqueous hydrochloric acid, providing 1.2 g (yield 74.6%) of the 4-[(methylsulfonyl)amino]benzoic acid. 1H NMR in d-chloroform: 8.03 (2H, d, J=8.7 Hz), 7.34 (2H, d, J=8.7 Hz), 3.09 (3H, s). 13C NMR in d-chloroform: 131.2, 117.9, 38.6.

Workup

  1. customSolvents were then removed
  2. customthe product purified by ethyl acetate extraction from 1N aqueous hydrochloric acid

Sources & evidence

ORD record
ord-f82e1be2368949ec859bab25801deb71
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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