Water → 1-Benzyl-1H-indole-5-carbonitrile

HRID 1361030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361030
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[H-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 27513Indole-5-carbonitrile

Produkt 1

HCID 161146831-Benzyl-1H-indole-5-carbonitrileAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Cyanoindole (1.0 g, 7.0 mmol) was dissolved in N,N-dimethylformamide (14 mL) and cooled in an ice-water bath. Sodium hydride (0.31 g, 60%, 7.8 mmol) was added, and the resulting suspension was stirred for 30 min. Benzyl chloride (0.85 mL, 0.94 g, 7.4 mmol) was added, and the cooling was discontinued. The stirring was continued for 65 hours at room temperature. Water (150 mL) was added, and the mixture was extracted with ethyl acetate (3×25 mL). The combined organic phases were washed with brine (30 mL) and dried with sodium sulfate (1 hour). Filtration and concentration yielded the crude material. Purification by flash chromatography on silica gel eluting with ethyl acetate/heptanes=1:3 afforded 1.60 g 1-benzyl-1H-indole-5-carbonitrile.

Aufarbeitung

  1. temperaturecooled in an ice-water bath
  2. waitThe stirring was continued for 65 hours at room temperature
  3. extractionthe mixture was extracted with ethyl acetate (3×25 mL)
  4. washThe combined organic phases were washed with brine (30 mL)
  5. dry with materialdried with sodium sulfate (1 hour)
  6. filtrationFiltration and concentration
  7. customyielded the crude material
  8. customPurification by flash chromatography on silica gel eluting with ethyl acetate/heptanes=1:3

Quellen und Nachweise

ORD-Eintrag
ord-64f854cb2e3e4171a602c7cf64ebaf36
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879893B2

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