Sodium Carbonate → 3-Amino-N-(4-bromo-phenyl)-4-(4-methanesulfonylamino-phenoxy)-benzamide

HRID 605138ノート

反応式

HRID 605138 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=3)=[C:12]([N+:28]([O-])=O)[CH:11]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.C(O)C.O.[Fe]>[NH2:28][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=1)[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)=[O:31]

参加物

7

反応物 2

HCID 10340Sodium CarbonateHCID 67040270N-(4-Bromo-phenyl)-4-(4-methanesulfonylamino-phenoxy)-3-nitro-benzamide

生成物 1

HCID 670406923-Amino-N-(4-bromo-phenyl)-4-(4-methanesulfonylamino-phenoxy)-benzamide収率 93%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A suspension of the product of Example 91B (223 mg, 0.4404 mmol) and iron powder (98 mg, 1.762 mmol) in acetic acid (5 mL) and ethanol (5 mL) was heated at reflux under a nitrogen atmosphere for 30 minutes. The reaction was cooled to room temperature, diluted with water (50 mL), and treated with solid sodium carbonate until the pH was 6. Extracted with ethyl acetate (100 mL), washed the organic with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation under vacuum. Co-evaporating the resulting oil with methylene chloride/hexanes gave the title compound as a light tan solid (195 mg, 93%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 30 minutes
  3. extractionExtracted with ethyl acetate (100 mL)
  4. washwashed the organic with brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation under vacuum
  8. customCo-evaporating the resulting oil with methylene chloride/hexanes

出典と根拠

ORDレコード
ord-6b93f1e1e8eb4e65bdb87f960f9731bb
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

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