Water → 4'-Cyano-N-ethyl-p-toluenesulfonanilide

HRID 1356698Notes

Reaction equation

HRID 1356698 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:21]=[CH:20][C:8]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:7][CH:6]=1)#[N:4].S(OCC)(O[CH2:26][CH3:27])(=O)=O.O>CN(C=O)C>[C:3]([C:5]1[CH:21]=[CH:20][C:8]([N:9]([CH2:26][CH3:27])[S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:7][CH:6]=1)#[N:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 257975n-(4-Cyanophenyl)-4-methylbenzenesulfonamide

Product 1

HCID 185093134'-Cyano-N-ethyl-p-toluenesulfonanilideYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (65%, 3.39 g (91.8 mmol)) in DMF (60.0 ml), 4′-cyano-p-toluenesulfonanilide (10.0 g (36.7 mmol)) was added with stirring at room temperature. To the resulting mixture, after stirring for an hour at room temperature, diethyl sulfate (12.0 ml (91.8 mmol)) was added dropwise, and the resulting mixture was heated with stirring at 75° C. for 4 hours. Then, the reaction mixture was allowed to cool to room temperature, poured into water and extracted with ethyl acetate. The extract was washed with dilute hydrochloric acid and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with chloroform as eluent, to give 9.8 g (89%) of the title compound as white crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after stirring for an hour at room temperature
  3. temperaturethe resulting mixture was heated
  4. stirringwith stirring at 75° C. for 4 hours
  5. temperatureto cool to room temperature
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with dilute hydrochloric acid
  8. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c398f769d0da432d93598f5a0e776f03
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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