1,2-Dibromoethane → 1-(Pyrazin-2-YL)cyclopropanecarbonitrile

HRID 931156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931156
[H-].[Na+].[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].Br[CH2:13][CH2:14]Br>CN(C)C=O>[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1([C:10]#[N:11])[CH2:14][CH2:13]1

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 12782906(Pyrazin-2-yl)acetonitrile

Produkt 1

HCID 584311071-(Pyrazin-2-YL)cyclopropanecarbonitrileAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (0.386 g, 16.1 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added dropwise a solution of 2-(pyrazin-2-yl)acetonitrile (0.55 g, 4.6 mmol) and 1,2-dibromoethane (2.25 g, 11.9 mmol) in anhydrous N,N-dimethylformamide (8 mL) over a period of 10 min at room temperature. The mixture was stirred for 18 h, then was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 100% dichloromethane) to afford 1-(pyrazin-2-yl)cyclopropanecarbonitrile (210 mg, 31%).

Aufarbeitung

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via column chromatography (100-200 mesh silica gel, 100% dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-035158bd72094f139941edfd772382ab
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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