Acetic Anhydride → N-acetyl-5-bromo-3-formyl-4-methoxybenzenesulfonamide

HRID 2069929

Reaction equation

HRID 2069929 reaction equation
[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH:12]=[O:13])[CH:5]=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.C(N(CC)CC)C.[C:23](OC(=O)C)(=[O:25])[CH3:24]>ClCCl>[C:23]([NH:11][S:8]([C:6]1[CH:7]=[C:2]([Br:1])[C:3]([O:14][CH3:15])=[C:4]([CH:12]=[O:13])[CH:5]=1)(=[O:10])=[O:9])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 866076983-Bromo-5-formyl-4-methoxy-benzenesulfonamide

Product 1

HCID 86607697N-acetyl-5-bromo-3-formyl-4-methoxybenzenesulfonamideYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100 mL round-bottom flask was charged with 5-bromo-3-formyl-4-methoxy-benzenesulfonamide (586 mg, 2.0 mmol) dissolved in dichloromethane (40 mL) and the solution was stirred vigorously while triethylamine (252 mg, 2.50 mmol) was added, followed by acetic anhydride (224 mg, 2.2 mmol) and a catalytic amount of N,N-dimethylaminopyridine. The mixture was stirred for 1 hour and then concentrated by evaporation. The residue was partitioned between 5% citric acid and ethyl acetate. The organic layer was separated, washed with water and brine and dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give N-acetyl-5-bromo-3-formyl-4-methoxybenzenesulfonamide (616 mg) as a white solid.

Workup

  1. additionwas added
  2. concentrationconcentrated by evaporation
  3. customThe residue was partitioned between 5% citric acid and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1d59530f5cc4a949793605c96991efa
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Linked notes

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