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

HRID 1747549

反応式

HRID 1747549 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2cb683ee343e423bb1693f9dfa14f8c6
出典データセット
uspto-grants-2015_10
特許番号
US09150569B2

関連ノート

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