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

HRID 1635705Notes

Reaction equation

HRID 1635705 reaction equation
C(=O)([O-])[O-].[Ca+2].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[CH3:17][C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([CH3:32])[C:24]=1[S:25]([CH2:28][N+:29]([O-:31])=[O:30])(=[O:27])=[O:26])[NH2:21].O>O1CCCC1>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:21][C:20]2[CH:19]=[C:18]([CH3:17])[C:24]([S:25]([CH2:28][N+:29]([O-:31])=[O:30])(=[O:27])=[O:26])=[C:23]([CH3:32])[CH:22]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 10112Calcium CarbonateHCID 195716Ici 222155

Product 1

HCID 186765404-bromo-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamideYield 24.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (20.0 mmol) of calcium carbonate and 3.8 g (14.9 mmol) of 4-bromobenzenesulphonyl chloride are successively added to a mixture of 2.4 g (9.83 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline in 45 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 20 h at room temperature and is then refluxed for 48 h. After cooling, it is poured into 400 ml of water and extracted with methylene chloride. The combined organic extracts are dried over sodium sulphate and concentrated to dryness under reduced pressure. The oily residue obtained is purified by chromatography on a column of silica (eluent: methylene chloride) to give 1.1 g (24%) of 4-bromo-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamide.

Workup

  1. temperatureis then refluxed for 48 h
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic extracts are dried over sodium sulphate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe oily residue obtained
  7. customis purified by chromatography on a column of silica (eluent: methylene chloride)

Sources & evidence

ORD record
ord-b40e833edb224f349c1bd9d6ac3cf4fd
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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