Water → 2'-Chloro-4'-cyano-N-ethyl-p-toluenesulfonanilide

HRID 1356671

Reaktionsgleichung

Reaktionsgleichung von HRID 1356671
[H-].[Na+].[Cl:3][C:4]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:5]=1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8].S(OCC)(O[CH2:27][CH3:28])(=O)=O.O>CN(C=O)C>[Cl:3][C:4]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:5]=1[N:6]([CH2:27][CH3:28])[S:7]([C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)(=[O:9])=[O:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 36959492'-Chloro-4'-cyano-p-toluenesulfonanilide

Produkt 1

HCID 185093272'-Chloro-4'-cyano-N-ethyl-p-toluenesulfonanilideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of sodium hydride (60%, 0.07 g (1.75 mmol)) in 3.0 ml of DMF, 2′-chloro-4′-cyano-p-toluenesulfonanilide (0.50 g (1.63 mmol)) was added under cooling with ice and with stirring. To the resulting mixture, after 15 minutes' stirring under cooling with ice, diethyl sulfate (0.25 ml (1.91 mmol)) was added dropwise and the mixture heated at 100° C. for 2 hours with stirring. Then, after being left to cool to room temperature, water was added and the mixture was extracted with diethyl ether. The extract was washed with water and 1% aqueous solution of sodium hydroxide, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting crystals were recrystallized from diethyl ether to give 0.33 g (61%) of the title compound as white crystals.

Aufarbeitung

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringTo the resulting mixture, after 15 minutes' stirring
  4. additionwas added dropwise
  5. stirringwith stirring
  6. waitThen, after being left
  7. temperatureto cool to room temperature
  8. extractionthe mixture was extracted with diethyl ether
  9. washThe extract was washed with water and 1% aqueous solution of sodium hydroxide
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting crystals were recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3b19cd9cd1b54d418c9387c265e0bf79
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586617B1

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