Imidazole → 5-(1H-imidazol-1-yl)picolinonitrile

HRID 2064231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064231
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>CN(C)C=O>[N:10]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Komponenten

4

Edukt 2

HCID 795ImidazoleHCID 8171545-Bromopyridine-2-carbonitrile

Produkt 1

HCID 671513405-(1H-imidazol-1-yl)picolinonitrileAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

5-bromopicolinonitrile (2.0 g, 10.9 mmol), imidazole (818 mg, 12 mmol) potassium carbonate (1.66 g, 12 mmol) and dimethylformamide (40 mL) were combined and heated to 130° C. for 20 hours. The reaction solution was evaporated and the residue was partitioned between dichloromethane (150 mL) and water (100 mL). The phases were separated and the organic phase was washed with water (50 mL), dried over magnesium sulfate and evaporated to give a residue which was purified by flash chromatography eluting with 2-3% methanol in dichloromethane gradient to give 5-(1H-imidazol-1-yl)picolinonitrile (1.23 g, 66%).

Aufarbeitung

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between dichloromethane (150 mL) and water (100 mL)
  3. customThe phases were separated
  4. washthe organic phase was washed with water (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give a residue which
  8. customwas purified by flash chromatography
  9. washeluting with 2-3% methanol in dichloromethane gradient

Quellen und Nachweise

ORD-Eintrag
ord-aaea9b01e3a544acab1acef278e29a01
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288405B2

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