Dimethylformamide → (1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetonitrile

HRID 349928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349928
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([CH2:19]Cl)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[K+].[CH3:24][N:25](C)C=O>O>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([CH2:19][C:24]#[N:25])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 230250441-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole

Produkt 1

HCID 23024861(1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetonitrileAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole (8.31 g), potassium cyanide (2.87 g), and N,N-dimethylformamide (100 ml) was stirred for 15 hours at 90° C., and poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and (1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetonitrile (3.50 g, yield: 44%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e94eaae61c404a3094fc68d0602349e7
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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