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

HRID 1747549

Reaction equation

HRID 1747549 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2cb683ee343e423bb1693f9dfa14f8c6
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Linked notes

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