Imidazole → 2-(2,4-dichlorobenzyloxy)-alpha-(1-imidazolyl)benzaldehyde O-methyloxime

HRID 128904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 128904
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH3:8][O:9][N:10]=[C:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27].CCOCC>CN(C=O)C>[CH3:8][O:9][N:10]=[C:11]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 53754588alpha-chloro-2-(2,4-dichlorobenzyloxy)benzaldehyde O-methyloxime

Produkt 1

HCID 542129432-(2,4-dichlorobenzyloxy)-alpha-(1-imidazolyl)benzaldehyde O-methyloximeAusbeute 48,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Imidazole (2.04 g) was dissolved in DMF (30 ml), and 60% sodium hydride (1.20 g) was added. The mixture was stirred at room temperature for 10 minutes, then α-chloro-2-(2,4-dichlorobenzyloxy)benzaldehyde O-methyloxime (5.17 g) was added, and the mixture was stirred at 120° C. for 2 hours. After completion of the reaction, ether (200 ml) was added, and the mixture was washed with brine (200 ml) twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography and recrystallized from ethyl acetate/n-hexane to give 2-(2,4-dichlorobenzyloxy)-α-(1-imidazolyl)benzaldehyde O-methyloxime (2.74 g) as colorless crystals. mp. 122°-123° C.

Aufarbeitung

  1. stirringthe mixture was stirred at 120° C. for 2 hours
  2. additionwas added
  3. washthe mixture was washed with brine (200 ml) twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel chromatography
  7. customrecrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-2b57d7bd540543fa9e4279011e8c16f3
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466661

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