Acetic Anhydride → 3-Nitro-N-(acetyl)benzenesulfonamide

HRID 1588038Notes

Reaction equation

HRID 1588038 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:14](OC(=O)C)(=[O:16])[CH3:15]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:13][C:14](=[O:16])[CH3:15])(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67138Benzenesulfonamide, 3-nitro-

Product 1

HCID 189578003-Nitro-N-(acetyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-nitrobenzenesulfonamide (615 mg) in 10 ml of dry tetrahydrofuran was cooled to 0° C. and mixed with 0.34 ml of acetic anhydride and 166 mg of 4-N,N-dimethylaminopyridine. The reaction mixture was stirred for 30 minutes, quenched with 10% citric acid solution, and diluted with ethyl acetate. The reaction mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried, concentrated in vacuo to yield 946 mg of the title compound in pure form.

Workup

  1. customquenched with 10% citric acid solution
  2. additiondiluted with ethyl acetate
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9387e865494f4e3ba1157d89058cb0af
Source dataset
uspto-grants-1993_06
Patent number
US05220018

Reaction notes

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