Benzoyl Peroxide → 3-Formyl-2-(4-methoxy-benzenesulfonylamino)-benzoic acid methyl ester

HRID 583383Notes

Reaction equation

HRID 583383 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13].C(OOC(=O)C1C=CC=CC=1)(=[O:31])C1C=CC=CC=1.BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:31])[C:5]=1[NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 158592082-(4-Methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl ester

Product 1

HCID 543619953-Formyl-2-(4-methoxy-benzenesulfonylamino)-benzoic acid methyl esterYield 165.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1.0 g (2.985 mmol) of the product of Example 3 in 100 mL of carbon tetrachloride was added 0.20 g of dibenzoyl peroxide and 1.168 g (6.568 mmol) of N-bromosuccinimide. The resulting mixture was refluxed for 18 h, cooled, washed with sodium bisulfite solution and water, dried over MgSO4, filtered and concentrated in vacuo. The residue was diluted with 10 mL of THF and 10 mL of 1N sodium hydroxide solution and the mixture was stirred at room temperature for 3 h. The reaction mixture was then acidified with 5% HCl and extracted with ether. The organics were dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether to provide 0.477 g (47%) of the product as a white solid. Electrospray Mass Spec: 350.1 (M+H)+.

Workup

  1. temperatureThe resulting mixture was refluxed for 18 h
  2. temperaturecooled
  3. washwashed with sodium bisulfite solution and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with 10 mL of THF and 10 mL of 1N sodium hydroxide solution
  8. extractionextracted with ether
  9. dry with materialThe organics were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-e18fa2d324a4447ea53ad42d909ff013
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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