Imidazole → 1-[2-(3-Chlorophenoxymethyl)-alpha-methoxyiminobenzyl]imidazole

HRID 279443Notes

Reaction equation

HRID 279443 reaction equation
CN(C)C=O.[H-].[Na+].[NH:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:30]=[CH:31][CH:32]=1)[O:17][CH2:18][C:19]1[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=1[C:21](Cl)=[N:22][O:23][CH3:24]>CCOCC>[Cl:13][C:14]1[CH:15]=[C:16]([CH:30]=[CH:31][CH:32]=1)[O:17][CH2:18][C:19]1[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=1[C:21]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)=[N:22][O:23][CH3:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 544326462-(3-Chlorophenoxymethyl)-alpha-methoxyiminobenzyl chloride

Product 1

HCID 539954371-[2-(3-Chlorophenoxymethyl)-alpha-methoxyiminobenzyl]imidazoleYield 65.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dimethylformamide (3 ml) and 60% sodium hydride (0.16 g, 3.9 mmol) were added to imidazole (0.27 g, 3.9 mmol), and the mixture was stirred at room temperature for 10 minutes. Then, 2-(3-chlorophenoxymethyl)-α-methoxyiminobenzyl chloride (0.40 g, 1.3 mmol) was added, and the mixture was stirred at 110° C. for 2 hours. After completion of the reaction, ether (100 ml) was added, and the mixture was washed with brine (80 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 1-[2-(3-chlorophenoxymethyl)-α-methoxyiminobenzyl]imidazole (0.29 g, 65.3%) as colorless crystals. mp. 96.5-97.5° C.

Workup

  1. stirringthe mixture was stirred at 110° C. for 2 hours
  2. additionwas added
  3. washthe mixture was washed with brine (80 ml) twice
  4. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  7. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-83aa2cd0f955485f870949d6486719a2
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

Loading…