Isatin → 1-Benzylisatin

HRID 365981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 365981
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 7054IsatinHCID 7498Benzyl BromideHCID 24758Sodium hydride

Produkt 1

HCID 2647341-BenzylisatinAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 44 g of isatin in 200 ml of N,N-dimethylformamide was added dropwise to a suspension of 16.0 g of sodium hydride (60%) in 100 ml of N,N-dimethylformamide at 0° C. in a nitrogen stream. After the mixture was stirred at that temperature for 30 minutes, a solution of 61.5 g of benzyl bromide in 100 ml of N,N-dimethylformamide was added thereto. The whole mixture was stirred for 1 hour and then concentrated. Chloroform was added to the residue, and the mixture was washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting crude product was washed with hexane and recrystallized from ethanol to give 47.3 g (67%) of the title compound as red needles.

Aufarbeitung

  1. stirringThe whole mixture was stirred for 1 hour
  2. concentrationconcentrated
  3. additionChloroform was added to the residue
  4. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washThe resulting crude product was washed with hexane
  8. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c1a6a6add9334a1589d1f65ee9061472
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127544

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