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Sodium Carbonate → 4-(5-Benzoylbenzimidazol-2-yl)-dimethylpyrrole-2-carboxylic acid

HRID 553238
ノート
印刷プレビュー

反応式

HRID 553238 の反応式
S([O-])(O)=O.[Na+].C([O:8][C:9]([C:11]1[NH:12][C:13]([CH3:19])=[C:14]([CH:17]=O)[C:15]=1[CH3:16])=[O:10])C.[NH2:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][C:34]=1[NH2:35])[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[C:24]([C:23]1[CH:32]=[CH:33][C:34]2[N:35]=[C:17]([C:14]3[C:15]([CH3:16])=[C:11]([C:9]([OH:8])=[O:10])[NH:12][C:13]=3[CH3:19])[NH:20][C:21]=2[CH:22]=1)(=[O:25])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 1355203,4-DiaminobenzophenoneHCID 1374862199-64-6HCID 23665763Sodium Bisulfite

生成物 1

HCID 160408334-(5-Benzoylbenzimidazol-2-yl)-dimethylpyrrole-2-carboxylic acid収率 90%

試薬・触媒・溶媒 1

HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
120 °C

実験手順

Sodium hydrogensulfite (1.0 g) and 3,5-dimethyl-4-formylpyrrole-2-carboxylic acid ethyl ester (1.5 g) were added to an N,N-dimethylacetamide (20 ml) solution of 3,4-diaminobenzophenone (1.6 g), and the mixture was heated to 120° C. and stirred for 10 hours. After the mixture was allowed to cool to room temperature, a 5% sodium carbonate (60 g) was added and stirred at room temperature, and the precipitate was collected by filtration and washed with water. The obtained solid was dissolved in ethanol (15 ml) and tetrahydrofuran (15 ml), and a 4 N sodium hydroxide aqueous solution (20 ml) was added and heated under reflux for 12 hours. After the starting material was disappeared, the reaction mixture was allowed to cool to room temperature, and neutralized with a 1 N hydrochloric acid solution. The precipitate was collected by filtration to afford 4-(5-benzoylbenzimidazol-2-yl)-dimethylpyrrole-2-carboxylic acid (2.3 g, 90%) as a light yellow solid.

後処理

  1. temperatureto cool to room temperature
  2. stirringstirred at room temperature
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. dissolutionThe obtained solid was dissolved in ethanol (15 ml)
  6. additiontetrahydrofuran (15 ml), and a 4 N sodium hydroxide aqueous solution (20 ml) was added
  7. temperatureheated
  8. temperatureunder reflux for 12 hours
  9. temperatureto cool to room temperature
  10. filtrationThe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-9c4ed00d41204e4ba00a11f8ac37f6c9
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07951956B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート