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

HRID 741710Notes

Reaction equation

HRID 741710 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-e032a2ccea1d40d4a71a4047a527a2cf
Source dataset
uspto-grants-1996_09
Patent number
US05552427

Reaction notes

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