Water → 2',4'-Dicyano-N-isopropyl-p-toluenesulfonanilide

HRID 1356654Notes

Reaction equation

HRID 1356654 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][C:6]=1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])#[N:4].[CH:24](I)([CH3:26])[CH3:25].O>CN(C=O)C>[C:3]([C:5]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][C:6]=1[N:7]([CH:24]([CH3:26])[CH3:25])[S:8]([C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1)(=[O:10])=[O:9])#[N:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 185093212',4'-Dicyano-p-toluenesulfonanilide

Product 1

HCID 185092342',4'-Dicyano-N-isopropyl-p-toluenesulfonanilideYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (65%, 0.12 g (3.30 mmol)) in 6.0 ml of DMF, 2′,4′-dicyano-p-toluenesulfonanilide (0.49 g (1.65 mmol)) was added with stirring at room temperature. To the resulting mixture, after 10 minutes' stirring at room temperature, isopropyl iodide (0.50 ml (4.94 mmol)) was added and the mixture was heated at 130° C. for 6 hours with stirring. The reaction mixture was then cooled to room temperature, poured into water and extracted with diethyl ether. The extract was washed with 1% aqueous sodium hydroxide solution and with 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 ethyl acetate-hexane (3:7) as eluent, to give 0.07 g (13%) of the title compound as white crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 10 minutes' stirring at room temperature
  3. temperaturethe mixture was heated at 130° C. for 6 hours
  4. stirringwith stirring
  5. temperatureThe reaction mixture was then cooled to room temperature
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with 1% aqueous sodium hydroxide solution and with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c24be3279884956ab81509a5f919717
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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