Sodium hydride → 1-(Pyrazin-2-yl)-1H-imidazole-4-carbaldehyde

HRID 50577

Reaktionsgleichung

Reaktionsgleichung von HRID 50577
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1.Cl[C:11]1[CH:16]=[N:15][CH:14]=[CH:13][N:12]=1>CN(C=O)C>[N:12]1[CH:13]=[CH:14][N:15]=[CH:16][C:11]=1[N:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 73277ChloropyrazineHCID 764281H-Imidazole-4-carbaldehyde

Produkt 1

HCID 227351831-(Pyrazin-2-yl)-1H-imidazole-4-carbaldehydeAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (60% in oil, 720 mg, 18.0 mmol) was added to a 0° C. solution of 1H-imidazole-4-carboxaldehyde (2.20 g, 18.0 mmol) in DMF (8 mL). After stirring for 20 min at 0° C., the mixture was allowed to warm to RT and a solution of 2-chloropyrazine (2.06 g, 17.9 mmol) in DMF (4 mL) was added. The resulting mixture was heated to 100° C. for 18 h. The solvent was evaporated, the residue was dissolved in ethyl acetate, washed with water and brine, dried (MgSO4), and concentrated to provide 3.10 g (86%) of the title compound. MS 175 (M+H)+

Aufarbeitung

  1. temperatureto warm to RT
  2. temperatureThe resulting mixture was heated to 100° C. for 18 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0326d4b48151442e9091b15321845211
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713455B2

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