Sodium Hydroxide → HCID 14771329, compound

HRID 476738Notes

Reaction equation

HRID 476738 reaction equation
[CH:1]1([S:7]([C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:31])C=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH:1]1([S:7]([C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[NH:18][S:19]([CH3:22])(=[O:20])=[O:21])(=[O:31])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 14771328HCID 14771328, compound

Product 1

HCID 14771329HCID 14771329, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 20 ml of a chloroform solution containing 1.2 g of N-(2-cyclohexylsulfinyl-4-nitrophenyl)methanesulfonamide obtained in Example 3 was added dropwise 60 ml of a chloroform solution containing 3.9 g of m-chloroperbenzoic acid under ice cooling with stirring. The mixture was stirred for 3 hours. The reaction solution was poured into ice water, neutralized with a dilute aqueous sodium hydroxide solution and extracted with chloroform. The chloroform layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated to give the crude crystals, which were washed with ethyl ether and then recrystallized from ethyl acetate-n-hexane to give 1.1 g of N-(2-cyclohexylsulfonyl-4-nitrophenyl)methanesulfonamide as pale yellow crystals.

Workup

  1. stirringThe mixture was stirred for 3 hours
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed, in turn, with water
  4. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give the crude crystals, which
  7. washwere washed with ethyl ether
  8. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-bf36b919a526479fb76c4f5f95e696b2
Source dataset
uspto-grants-1989_12
Patent number
US04885367

Reaction notes

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