Imidazole → Ethyl p-(1-imidazolyl)acetylaminobenzoate

HRID 1249545ノート

反応式

HRID 1249545 の反応式
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH2:9][C:10]([NH: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:11]>CN(C)C=O>[N:3]1([CH2:9][C:10]([NH:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=2)=[O:11])[CH:7]=[CH:6][N:5]=[CH:4]1

参加物

5

反応物 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 244075Ethyl 4-[(chloroacetyl)amino]benzoate

生成物 1

HCID 13750113Ethyl p-(1-imidazolyl)acetylaminobenzoate収率 76.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

To a suspension of 2.4 g of 50% sodium hydride in 100 ml of dry dimethylformamide was added slowly 3.4 g of imidazole at room temperature, and the mixture was heated to 80° C. A solution of 12.1 g of ethyl p-chloroacetylaminobenzoate in 45 ml of dry dimethylformamide was added to the mixture over a period of 30 minutes at 80° C., and then the reaction mixture was heated at 100° C. for 1.5 hours. After removal of the solvent under reduced pressure, the residue was dissolved in chloroform and washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residual solid was recrystallized from ethanol-n-hexane to give 10.5 g of ethyl p-(1-imidazolyl)acetylaminobenzoate as colorless needles. M.P.: 185°-187° C.

後処理

  1. temperaturethe reaction mixture was heated at 100° C. for 1.5 hours
  2. customAfter removal of the solvent under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residual solid was recrystallized from ethanol-n-hexane

出典と根拠

ORDレコード
ord-021e87cfb686432f98787d2382cc3edb
出典データセット
uspto-grants-1986_12
特許番号
US04632934

反応ノート

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