4-Aminothiophenol → 4-(4-Amino-phenylsulfanyl)-N-(4-bromo-phenyl)-3-nitro-benzamide

HRID 605054

Reaction equation

HRID 605054 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13](Cl)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+]>C(O)C>[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][C:13]2[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[O:20])=[CH:11][C:12]=2[N+:17]([O-:19])=[O:18])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 145104-AminothiophenolHCID 517045Sodium AcetateHCID 1068537N-(4-bromophenyl)-4-chloro-3-nitrobenzamide

Product 1

HCID 670408504-(4-Amino-phenylsulfanyl)-N-(4-bromo-phenyl)-3-nitro-benzamideYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product of Example 10A (1.00 g, 2.816 mmol), 4-aminothiophenol (529 mg, 4.224 mmol) and anhydrous sodium acetate (1.155 g, 14.08 mmol) in anhydrous ethanol (30 mL) was heated at reflux under a nitrogen atmosphere for 19 hours. The reaction was cooled to room temperature and the ethanol removed by rotary evaporation. The residue was taken up in water (50 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Trituration of the solid with 4% ethyl acetate/methylene chloride (25 mL) afforded the title compound as a yellow solid (1.091 g, 87%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 19 hours
  3. customthe ethanol removed by rotary evaporation
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washThe combined organic extracts were washed with brine (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6cd7585c1f84199a0a4c25985e5e4a4
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Linked notes

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