Cesium carbonate → N-(4-Bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-nitro-benzamide

HRID 605071Notes

Reaction equation

HRID 605071 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.[SH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[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]([S:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2401474-MercaptophenolHCID 1068537N-(4-bromophenyl)-4-chloro-3-nitrobenzamide

Product 1

HCID 67040744N-(4-Bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-nitro-benzamideYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product of Example 10A (553 mg, 1.557 mmol) in anhydrous N,N-dimethylformamide (15 mL) was treated with 4-mercaptophenol (196 mg, 1.557 mmol) and cesium carbonate (1.015 g, 3.114 mmol) at room temperature, then heated at 100° under a nitrogen atmosphere for 3 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. The residue was taken up in H2O (30 mL) and the pH adjusted to 3 with 1N aqueous HCl. The aqueous was extracted with ethyl acetate (2×50 mL), and the combined organic extracts washed with brine (25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation. The residue was purified by trituration with methylene chloride and silica gel flash chromatography with a gradient of 6% to 30% ethyl acetate/methylene chloride to give the product as a dark yellow solid (517 mg, 75%).

Workup

  1. temperatureheated at 100° under a nitrogen atmosphere for 3 hours
  2. customthe solvent removed by rotary evaporation in vacuo
  3. extractionThe aqueous was extracted with ethyl acetate (2×50 mL)
  4. washthe combined organic extracts washed with brine (25 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by trituration with methylene chloride and silica gel flash chromatography with a gradient of 6% to 30% ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-9be9449b2904441590dc184fc768bf61
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…