Acetic Anhydride → 3-acetamidobenzenesulfonic acid

HRID 1957389Notes

Reaction equation

HRID 1957389 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([OH:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18]>O1CCCC1.O>[C:17]([NH:1][C:2]1[CH:3]=[C:4]([S:8]([OH:11])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 84743-Aminobenzenesulfonic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 17138393-acetamidobenzenesulfonic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 1.48 g of 3-aminobenzene sulfonic acid in 1:1 tetrahydrofuran/water was treated at 0° C. with 1.43 g of sodium bicarbonate. After 5 min, 1.30 g of acetic anhydride was added dropwise and the reaction allowed to warm to ambient temperature under an atmosphere of nitrogen over 14 h. The reaction mixture was passed through a column of Amberlyst 15 ion exchange resin, eluted with water, and concentrated in vacuo to yield an oil which upon treatment with benzene and azeotropic removal of water in vacuo yielded 1.8 g of the title product as a white crystalline solid. (1H)-NMR (CDCl3) consistent with structure.

Workup

  1. washeluted with water
  2. concentrationconcentrated in vacuo
  3. customto yield an oil which upon treatment
  4. customwith benzene and azeotropic removal of water in vacuo

Sources & evidence

ORD record
ord-350f14e372b642c7a9fcf3708c74874a
Source dataset
uspto-grants-1998_07
Patent number
US05783701

Reaction notes

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