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

HRID 605138Notes

Reaction equation

HRID 605138 reaction equation
[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]

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-6b93f1e1e8eb4e65bdb87f960f9731bb
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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