Imidazole → 1-[3-(4-Ethoxycarbonylphenoxy)propyl]imidazole

HRID 745927노트

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HRID 745927 반응식
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1.O>CN(C)C=O>[CH2:20]([O:19][C:17]([C:16]1[CH:22]=[CH:23][C:13]([O:12][CH2:11][CH2:10][CH2:9][N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)=[CH:14][CH:15]=1)=[O:18])[CH3:21]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydride2회HCID 18348522Ethyl 4-(3-chloropropoxy)benzoate

생성물 1

HCID 135691811-[3-(4-Ethoxycarbonylphenoxy)propyl]imidazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

Sodium hydride (0.6 g, 50% suspension in mineral oil) was added cautiously to a stirred and cooled solution of imidazole (0.79 g) in dry N,N-dimethylformamide (50 ml). After the initial vigorous reaction had subsided the mixture was heated to 100° C. for 10 minutes and then stirred at room temperature for a further 1 hour. Ethyl 4-(3-chloropropoxy)benzoate (2.8 g) was added over 2 minutes and the resulting mixture was heated on a steam bath for 6 hours and then cooled. Water (1 ml) was added to decompose any unreacted sodium hydride and the solution was evaporated and the residue was chromatographed on silica gel. Elution with chloroform gave mineral oil and small amounts of impurity. Elution with chloroform/methanol (20:1) gave the pure 1-[3-(4-ethoxycarbonylphenoxy)propyl]imidazole as an oil on evaporation of the solvent.

후처리

  1. customAfter the initial vigorous reaction
  2. stirringstirred at room temperature for a further 1 hour
  3. temperaturethe resulting mixture was heated on a steam bath for 6 hours
  4. temperaturecooled
  5. customthe solution was evaporated
  6. customthe residue was chromatographed on silica gel
  7. washElution with chloroform
  8. customgave mineral oil and small amounts of impurity
  9. washElution with chloroform/methanol (20:1)

출처 및 근거

ORD 기록
ord-5e11406b07c84e408a86c268d4ce1322
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04602016

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