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

HRID 741710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 741710
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 67740611N-(1-methylimidazol-2-yl)-4-methoxybenzylideneamine hydrochlorideAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e032a2ccea1d40d4a71a4047a527a2cf
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552427

Notizen zur Reaktion

Wird geladen…