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

HRID 1356698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356698
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c398f769d0da432d93598f5a0e776f03
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586617B1

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