Pyridine → 4-bromo-2,5-difluoro-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamide

HRID 1635711Notes

Reaction equation

HRID 1635711 reaction equation
N1C=CC=CC=1.[OH-].[K+].[Br:9][C:10]1[C:15]([F:16])=[CH:14][C:13]([S:17](Cl)(=[O:19])=[O:18])=[C:12]([F:21])[CH:11]=1.[CH3:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([CH3:37])[C:29]=1[S:30]([CH2:33][N+:34]([O-:36])=[O:35])(=[O:32])=[O:31])[NH2:26]>O1CCCC1.O>[Br:9][C:10]1[C:15]([F:16])=[CH:14][C:13]([S:17]([NH:26][C:25]2[CH:24]=[C:23]([CH3:22])[C:29]([S:30]([CH2:33][N+:34]([O-:36])=[O:35])(=[O:32])=[O:31])=[C:28]([CH3:37])[CH:27]=2)(=[O:19])=[O:18])=[C:12]([F:21])[CH:11]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 14797Potassium HydroxideHCID 195716Ici 222155HCID 5745904-Bromo-2,5-difluorobenzenesulfonyl Chloride

Product 1

HCID 186765374-bromo-2,5-difluoro-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamideYield 6.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.3 g (16.4 mmol) of pyridine, dried over potassium hydroxide, and then 3.6 g (12.3 mmol) of 4-bromo-2,5-difluorobenzenesulphonyl chloride are added to a solution, maintained under a nitrogen atmosphere, of 2.0 g (8.19 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline in 40 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 7 h 30 min at room temperature and then for 11 h at reflux; after cooling, it is poured into 300 ml of water and extracted 3 times with methylene chloride. The combined organic extracts are washed with water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The solid residue obtained is purified by chromatography on a column of silica (eluent: methylene chloride) and recrystallization from a mixture of hexane and ethyl acetate, to give 0.24 g (6.2%) of 4-bromo-2,5-difluoro-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamide, containing 5 mol % of ethyl acetate.

Workup

  1. temperaturefor 11 h at reflux
  2. temperatureafter cooling
  3. extractionextracted 3 times with methylene chloride
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe solid residue obtained
  8. customis purified by chromatography on a column of silica (eluent: methylene chloride) and recrystallization from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-52f87d0317564daa95df99bf9eaca6ed
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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