Water → 1H-Benzimidazole-2-acetonitrile, 1-methyl-

HRID 1787711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1787711
CI.[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12][C:13]#[N:14].[C:15](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.CO>[CH3:15][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12][C:13]#[N:14]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 204551H-Benzimidazole-2-acetonitrile

Produkt 1

HCID 759531H-Benzimidazole-2-acetonitrile, 1-methyl-Ausbeute 14,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl iodide (1.24 ml, 19.19 mmol) is added to a solution of (1H-benzoimidazol-2-yl)-acetonitrile (3.13 g, 19.91 mmol) and potassium carbonate (2.75 g, 19.91 mmol) in 20 ml of dimethylformamide. It is stirred for 24 hours at room temperature, and additional potassium carbonate (2.8 g, 20.27 mmol) and additional methyl iodide (1.3 ml, 20.12 mmol) are added. It is stirred for another 24 hours at room temperature, water and methanol are added, and the solvent is distilled off in a vacuum. The residue is mixed with 200 ml of water and extracted three times in succession with 200 ml each of dichloromethane. The combined organic phases are dried on sodium sulfate, concentrated by evaporation, and after purification by chromatography on silica gel, 502 mg of the title compound is obtained.

Aufarbeitung

  1. stirringIt is stirred for another 24 hours at room temperature
  2. distillationthe solvent is distilled off in a vacuum
  3. additionThe residue is mixed with 200 ml of water
  4. extractionextracted three times in succession with 200 ml each of dichloromethane
  5. customThe combined organic phases are dried on sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customafter purification by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b17c81b7874f4b43b33907bc4cd8ca31
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511059B2

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