Methyl p-toluenesulfonate → 1,2-dimethyl-1H-imidazole-5-carbaldehyde

HRID 1747549

Reaktionsgleichung

Reaktionsgleichung von HRID 1747549
[CH3:1][C:2]1[NH:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1.[C:9](=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(OC)(=O)=O)=CC=1.[OH-].[Na+]>CN(C=O)C.O>[CH3:9][N:3]1[C:4]([CH:7]=[O:8])=[CH:5][N:6]=[C:2]1[CH3:1]

Komponenten

7

Edukt 4

HCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 27958782-Methyl-1H-imidazole-4-carboxaldehyde

Produkt 1

HCID 31596101,2-dimethyl-1H-imidazole-5-carbaldehydeAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In DMF (10 mL) was dissolved 2-methyl-1H-imidazole-5-carbaldehyde (1.00 g, 9.08 mmol). Potassium carbonate (2.51 g, 18.2 mmol) and methyl p-toluenesulfonate (2.06 mL, 13.6 mmol) were added under ice-cooling and the mixture was stirred at room temperature for 6 hours. A 1 mol/L aqueous sodium hydroxide solution and water were added to the reaction mixture. Extraction with ethyl acetate, washing with a 1 mol/L aqueous sodium hydroxide solution and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=19/1) to give 1,2-dimethyl-1H-imidazole-5-carbaldehyde (180 mg, 16% yield).

Aufarbeitung

  1. temperaturecooling
  2. extractionExtraction with ethyl acetate
  3. washwashing with a 1 mol/L aqueous sodium hydroxide solution
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=19/1)

Quellen und Nachweise

ORD-Eintrag
ord-2cb683ee343e423bb1693f9dfa14f8c6
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150569B2

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