Ethanol → HCID 178469892、化合物

HRID 538840ノート

反応式

HRID 538840 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11]O)=[NH:10])=[CH:4][CH:3]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[C:14]#[CH:15].CCO.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH2:18]([O:17][C:13]([C:14]1[N:10]=[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[NH:11][CH:15]=1)=[O:16])[CH3:19]

参加物

5

反応物 4

HCID 702EthanolHCID 7583Diphenyl EtherHCID 12182Ethyl propiolateHCID 178510745HCID 178510745、化合物

生成物 1

HCID 178469892HCID 178469892、化合物収率 49%

反応条件

温度
190 °C

実験手順

2-(4-bromophenyl)-N-hydroxyacetamidine (5.0 g, 21.8 mmol) and ethyl propiolate (2.4 mL, 24.0 mmol) were dissolved in EtOH (100 mL, 2 mol). The mixture was heated to reflux for 7 hours, cooled and then concentrated. The residue was then dissolved in diphenyl ether (75 mL, 470 mmol), heated at 190° C. for 2 hours, cooled, combined with 400 mL of hexanes, and allowed to sit overnight. The solvent was decanted and the precipitant was dissolved in DCM and purified by column chromatography (0-10% MeOH in DCM) to yield 2-(4-bromobenzyl)-1H-imidazole-4-carboxylic acid ethyl ester (3.3 g).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 7 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. temperaturecooled
  6. customThe solvent was decanted
  7. dissolutionthe precipitant was dissolved in DCM
  8. custompurified by column chromatography (0-10% MeOH in DCM)

出典と根拠

ORDレコード
ord-9e67113720b34e089758ba0c982d25d2
出典データセット
uspto-grants-2014_10
特許番号
US08865755B2

反応ノート

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