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

HRID 279443노트

반응식

HRID 279443 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-83aa2cd0f955485f870949d6486719a2
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362212B1

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