Acetic Anhydride → 4-Sulfamoylphenyl acetate

HRID 2099547Notes

Reaction equation

HRID 2099547 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>O>[S:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][C:14](=[O:16])[CH3:15])=[CH:5][CH:6]=1)(=[O:11])(=[O:12])[NH2:13]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 74093p-Hydroxybenzenesulfonamide

Product 1

HCID 597731074-Sulfamoylphenyl acetateYield 55.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium hydroxide (116 mg, 2.9 mmoles) in water (10 ml) was added to a stirred solution of 4-hydroxy-benzenesulphonamide (500 mg, 2.9 mmoles) in water (30 ml). This mixture was treated with acetic anhydride (295 mg, 2.9 mmoles) and stirred at room temperature for 4.5 hours. The reaction mixture was filtered off and the resulting solid washed with water to afford acetic acid 4-sulphamoyl-phenyl ester (33)(348 mg) as a yellow solid. LC/MS System A; Rt 2.06 mins.

Workup

  1. filtrationThe reaction mixture was filtered off
  2. washthe resulting solid washed with water

Sources & evidence

ORD record
ord-02713c1aac0a4081ad9706cfba118b2c
Source dataset
uspto-grants-2009_08
Patent number
US07569602B2

Reaction notes

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