Thiophenol → 5-Chloro-2-hydroxy-N-methyl-benzenesulfonamide

HRID 480201Notes

Reaction equation

HRID 480201 reaction equation
[H-].[Na+].C1(S)C=CC=CC=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:22]C)=[C:15]([S:17]([NH:20][CH3:21])(=[O:19])=[O:18])[CH:16]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([OH:22])=[C:15]([S:17]([NH:20][CH3:21])(=[O:18])=[O:19])[CH:16]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 29878855-chloro-2-methoxy-N-methylbenzenesulfonamide

Product 1

HCID 187681025-Chloro-2-hydroxy-N-methyl-benzenesulfonamideYield 64.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium hydride (60% in mineral oil, 90.24 mg, 2.25 mmol) in dry dimethyl formamide was added thiophenol (0.225 ml, 2.25 mmol) dropwise. To this was then added 5-Chloro-2-methoxy-N-methyl-benzenesulfonamide (531 mg, 2.25 mmol) followed by refluxing for 4 hours. The reaction mixture was cooled, diluted with ethyl acetate and washed with a 1N sulfuric acid solution. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel yielded the above titled compound (320 mg, 53% yield).

Workup

  1. temperatureby refluxing for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. washwashed with a 1N sulfuric acid solution
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d3749d4f25943e7b04a0ddc71f49585
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

Loading…