4-Methoxybenzaldehyde → N-(1-methylimidazol-2-yl)-4-methoxybenzylideneamine hydrochloride

HRID 741710ノート

反応式

HRID 741710 の反応式
[ClH:1].[NH2:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=1.C[O-].[Na+].[CH:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1>C(O)C>[ClH:1].[CH3:8][N:4]1[CH:5]=[CH:6][N:7]=[C:3]1[N:2]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 312444-MethoxybenzaldehydeHCID 101540761-Methyl-1H-imidazol-2-amine hydrochlorideHCID 10942334Sodium Methoxide

生成物 1

HCID 67740611N-(1-methylimidazol-2-yl)-4-methoxybenzylideneamine hydrochloride収率 30.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-Amino-1-methylimidazole hydrochloride (0.3 g) was dissolved in ethanol (4 ml), and sodium methoxide (28% methanol solution: 0.5 ml) and p-anisaldehyde (0.34 g) were added. The mixture was heated at reflux overnight. The solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: methanol-chloroform=5:95), and the solvent in the desired fraction was evaporated. The precipitated pale yellow prisms were separated by filtration using hexane. The resulting crystals were dissolved in chloroform, and 4N hydrochloric acid--ethyl acetate (0.22 ml) was added. The solvent was evaporated, and the precipitated pale yellow was separated by filtration using diethyl ether to give the title compound (0.17 g, 26.9%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography (eluent: methanol-chloroform=5:95)
  5. customthe solvent in the desired fraction was evaporated
  6. customThe precipitated pale yellow prisms were separated by filtration
  7. dissolutionThe resulting crystals were dissolved in chloroform
  8. addition4N hydrochloric acid--ethyl acetate (0.22 ml) was added
  9. customThe solvent was evaporated
  10. customthe precipitated pale yellow was separated by filtration

出典と根拠

ORDレコード
ord-e032a2ccea1d40d4a71a4047a527a2cf
出典データセット
uspto-grants-1996_09
特許番号
US05552427

反応ノート

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