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

HRID 1747549

반응식

HRID 1747549 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2cb683ee343e423bb1693f9dfa14f8c6
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150569B2

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