Water → 1-Methyl-2-nitro-4-(phenylsulfonyl)benzene

HRID 2390196Notes

Reaction equation

HRID 2390196 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[OH:18]OS([O-])=O.[K+].[OH2:24]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:18])=[O:24])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 565939751-Methyl-2-nitro-4-(phenylthio)benzene2×

Product 1

HCID 565939761-Methyl-2-nitro-4-(phenylsulfonyl)benzeneYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-methyl-2-nitro-4-(phenylthio)benzene (Intermediate 111; 745 mg; 3.04 mmol) in MeOH (11 ml) and water (11 ml) was treated with Oxone® (5.60 g; 9.11 mmol) and the reaction mixture was stirred at RT for 6 hours. Water was added and the reaction mixture was extracted 2 times with DCM. The combined organic extracts were dried over MgSO4, filtered and concentrated to dryness affording the title compound as a beige solid (690 mg, 82%).

Workup

  1. extractionthe reaction mixture was extracted 2 times with DCM
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4c7a111b1edd414a89f9f07d56f679e5
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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