Hydrogen Peroxide → Methanesulfonamide, 1-[(3,4-dichlorophenyl)sulfinyl]-

HRID 1288093Notes

Reaction equation

HRID 1288093 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][S:11]([NH2:14])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:15]O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:10][S:11]([NH2:14])(=[O:12])=[O:13])=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 12268475Methanesulfonamide, 1-[(3,4-dichlorophenyl)thio]-

Product 1

HCID 12268493Methanesulfonamide, 1-[(3,4-dichlorophenyl)sulfinyl]-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 0.50 g. (0.0018 mol.) of 1-((3,4-dichlorophenyl)thio)methanesulfonamide in 25 ml. of glacial acetic acid is added 0.10 g. of 30% hydrogen peroxide, and the reaction mixture is heated at 65° to 70° C. The progress of the reaction is followed by nuclear magnetic resonance spectroscopy, and over a period of 7 hours an additional 0.37 g. of 30% hydrogen peroxide is added in small incremental amounts. After the 7 hour reaction period, the acetic acid solution is allowed to cool, and the title compound separates as fluffy, white crystals. The crystals are filtered, washed with ether, and dried to give 0.37 g. of 1-((3,4-dichlorophenyl)sulfinyl)methanesulfonamide, m.p. 205°-207° C.

Workup

  1. customAfter the 7 hour reaction period
  2. temperatureto cool

Sources & evidence

ORD record
ord-ba938b032e0d4329b35bfd6928a59b4b
Source dataset
uspto-grants-1976_10
Patent number
US03987095

Reaction notes

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