m-Chloroperbenzoic acid → HCID 15859748, compound

HRID 1635700Notes

Reaction equation

HRID 1635700 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:14]=[C:15]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:16]=[C:17]([CH3:24])[C:18]=1[S:19][CH2:20][N+:21]([O-:23])=[O:22].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:12][C:13]1[CH:14]=[C:15]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:27])=[O:28])[CH:16]=[C:17]([CH3:24])[C:18]=1[S:19]([CH2:20][N+:21]([O-:23])=[O:22])=[O:9]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 15859747HCID 15859747, compound

Product 1

HCID 15859748HCID 15859748, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.3 g (5.46 mmol) of 70-75% m-chloroperbenzoic acid are added rapidly to a solution of 2.2 g (6.24 mmol) of N-[3,5-dimethyl-4-[(nitromethyl)thio]phenyl]benzenesulphonamide in 79 ml of anhydrous chloroform. The reaction medium is stirred for 24 h at room temperature and then poured into a solution of 0.33 g (3.93 mmol) of sodium bicarbonate. The mixture is extracted with methylene chloride. The combined organic extracts are dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue obtained is purified by successive chromatographies on a column of silica (eluent for the first chromatography: methylene chloride; eluent for the second chromatography; 2/1 hexane/ethyl acetate) and crystallization from hexane, to give 0.98 g (42%) of N-[3,5-dimethyl-4-[(nitromethyl)sulphinyl]phenyl]benzenesulphonamide.

Workup

  1. extractionThe mixture is extracted with methylene chloride
  2. dry with materialThe combined organic extracts are dried over sodium sulphate
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue obtained
  5. customis purified by successive chromatographies on a column of silica (eluent for the first chromatography
  6. custom2/1 hexane/ethyl acetate) and crystallization from hexane

Sources & evidence

ORD record
ord-fb4986dbf2de46ddbb4e64ed3312480a
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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