HCID 668793, compound → Benzenesulfonamide, 4-hydroxy-N,N-dimethyl-

HRID 1030206Notes

Reaction equation

HRID 1030206 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 668793HCID 668793, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 84760Benzenesulfonamide, 4-hydroxy-N,N-dimethyl-Yield 75.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-methoxy-N,N-dimethylbenzenesulfonamide (37 g) and aluminum chloride (69 g) in benzene (170 ml) was stirred under reflux for 30 minutes. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by recrystallization from toluene to give 4-hydroxy-N,N-dimethylbenzenesulfonamide (26 g).

Workup

  1. temperatureunder reflux for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization from toluene

Sources & evidence

ORD record
ord-a7aa49b1789841658b301a6856c6a887
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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