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

HRID 128904Notes

Reaction equation

HRID 128904 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 542129432-(2,4-dichlorobenzyloxy)-alpha-(1-imidazolyl)benzaldehyde O-methyloximeYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2b57d7bd540543fa9e4279011e8c16f3
Source dataset
uspto-grants-1995_11
Patent number
US05466661

Reaction notes

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