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

HRID 745927ノート

反応式

HRID 745927 の反応式
[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]

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydride2 回HCID 18348522Ethyl 4-(3-chloropropoxy)benzoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5e11406b07c84e408a86c268d4ce1322
出典データセット
uspto-grants-1986_07
特許番号
US04602016

反応ノート

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