Water → HCID 18509228, Verbindung

HRID 1356630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356630
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([N+:12]([O-:14])=[O:13])[C:7]([NH:10][CH3:11])=[N:8][CH:9]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([N+:12]([O-:14])=[O:13])[C:7]([N:10]([CH3:11])[S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])=[N:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 4054585HCID 4054585, Verbindung

Produkt 1

HCID 18509228HCID 18509228, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (60%, 0.05 g (1.25 mmol)) in 2.0 ml of DMF, 5-chloro-2-methylamino-3-nitropyridine (0.20 g (1.07 mmol)) was added under cooling with ice and with stirring. To the resulting mixture, after 15 minutes' stirring under cooling with ice, p-toluenesulfonyl chloride (0.23 g (1.21 mmol)) was added. The reaction mixture was stirred under cooling with ice for 30 minutes and then at room temperature for 30 minutes, poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was then subjected to silica gel column chromatography with ethyl acetate-hexane (1:3) as eluent, to give 0.16 g (44%) of the title compound as pale yellow crystals.

Aufarbeitung

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringTo the resulting mixture, after 15 minutes' stirring
  4. additionwas added
  5. stirringThe reaction mixture was stirred
  6. temperatureunder cooling with ice for 30 minutes
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water and saturated sodium chloride solution
  9. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fe965bd425ec4235906c28ff777e1ac1
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586617B1

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