Azobisisobutyronitrile → 5-Bromo-2-(4-methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl ester

HRID 583298Notes

Reaction equation

HRID 583298 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].[Br:24]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([Br:24])[CH:7]=[C:6]([CH3:10])[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

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 158592082-(4-Methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl ester

Product 1

HCID 542183595-Bromo-2-(4-methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl esterYield 50.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 1.00 g (2.985 mmol) of the product of Example 3 in 100 mL of CHCl3 was added 0.531 g (2.985 mmol) of N-bromosuccinimide and 0.025 g of AIBN. The resulting mixture was heated to reflux for 18 h and then an additional 0.411 g of NBS and 0.013 g of AIBN were added to the reaction. After refluxing the reaction for another 5 h the reaction mixture was cooled to room temperature, washed with sodium sulfite solution and water, dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether-hexanes to provide 0.62 g (50%) of the desired product as a white solid. EI Mass Spec 413 (M+).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 18 h
  3. temperatureAfter refluxing
  4. customthe reaction for another 5 h the reaction mixture
  5. washwashed with sodium sulfite solution and water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether-hexanes

Sources & evidence

ORD record
ord-085326c50a0e445a871417dbdf2d83c2
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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