Dimethylformamide → 2-(4-bromobenzyl)-1-propyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 659662ノート

反応式

HRID 659662 の反応式
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH3:10].[CH2:11]([O:13][C:14]([C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)[NH:19][CH:20]=1)=[O:15])[CH3:12].CN(C=O)C>CCOC(C)=O>[CH2:11]([O:13][C:14]([C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Br:28])=[CH:26][CH:27]=2)[N:19]([CH2:8][CH2:9][CH3:10])[CH:20]=1)=[O:15])[CH3:12].[CH2:11]([O:13][C:14]([C:16]1[N:17]([CH2:8][CH2:9][CH3:10])[C:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Br:28])=[CH:26][CH:27]=2)=[N:19][CH:20]=1)=[O:15])[CH3:12]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178469892HCID 178469892、化合物

生成物 2

HCID 580889072-(4-bromobenzyl)-1-propyl-1H-imidazole-4-carboxylic acid ethyl ester収率 33.6%HCID 672311902-(4-bromobenzyl)-3-propyl-3H-imidazole-4-carboxylic acid ethyl ester収率 20%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

Potassium carbonate (2.6 g, 18.7 mmol) and 1-iodopropane (669.7 μL, 6.9 mmol) were added to 2-(4-Bromobenzyl)-1H-imidazole-4-carboxylic acid ethyl ester (1.9 g, 6.2 mmol) dissolved in DMF (40 mL, 500 mmol). The mixture was heated at 60° C. for 5 hours. The mixture was cooled and then diluted with EtOAc (100 mL), washed with water and saturated aqueous NaCl (100 mL each), dried over MgSO4, filtered and concentrated. The mixture was purified by column chromatography (20-60% EtOAc in Hexanes) to yield the desired product, 2-(4-bromobenzyl)-1-propyl-1H-imidazole-4-carboxylic acid ethyl ester (736 mg, 33.6% yield), and its regioisomer, 2-(4-bromobenzyl)-3-propyl-3H-imidazole-4-carboxylic acid ethyl ester (500 mg, 20% yield). The structures were confirmed by NMR.

後処理

  1. temperatureThe mixture was cooled
  2. washwashed with water and saturated aqueous NaCl (100 mL each)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture was purified by column chromatography (20-60% EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-6ddb51a010554335bffdf642768ea0a2
出典データセット
uspto-grants-2011_12
特許番号
US08080572B2

反応ノート

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