Water → HCID 15859749, compound

HRID 1635701Notes

Reaction equation

HRID 1635701 reaction equation
C(=O)([O-])[O-].[Ca+2].[Cl: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>[Cl: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 73984-Chlorobenzenesulfonyl chlorideHCID 10112Calcium CarbonateHCID 195716Ici 222155

Product 1

HCID 15859749HCID 15859749, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.45 g (14.5 mmol) of calcium carbonate and then 2.3 g (10.9 mmol) of 4-chlorobenzenesulphonyl chloride are successively added to a mixture of 1.8 g (7.37 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline in 45 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 27 h at room temperature and then poured into 200 ml of water. This mixture is 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 residue obtained is purified by chromatography on a column of silica (eluent: methylene chloride) and then by recrystallization from chloroform, to give 0.44 g (14%) of 4-chloro-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamide.

Workup

  1. extractionThis mixture is extracted 3 times with methylene chloride
  2. washThe combined organic extracts are washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica (eluent: methylene chloride)
  7. customby recrystallization from chloroform

Sources & evidence

ORD record
ord-8f535083f15a442998f48e48f4cfb9ce
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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