Potassium Permanganate → 1,2-Benzisothiazol-3(2H)-one, 5,6-dimethoxy-, 1,1-dioxide

HRID 259533Notes

Reaction equation

HRID 259533 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13].[Mn]([O-])(=O)(=O)=[O:17].[K+]>[OH-].[Na+]>[CH3:9][O:8][C:6]1[C:5]([O:10][CH3:11])=[CH:4][C:3]2[S:12](=[O:14])(=[O:13])[NH:15][C:1](=[O:17])[C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 352990334,5-Dimethoxy-2-methylbenzene-1-sulfonamide

Product 1

HCID 470031361,2-Benzisothiazol-3(2H)-one, 5,6-dimethoxy-, 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

16 gm (0.08 mol) of 2-methyl-4,5-dimethoxy-benzene sulfonamide were dissolved in 500 ml of an aqueous 5% sodium hydroxide solution, and the solution was heated at its boiling point for 2 hours after addition of 39.6 gm (0.25 mol) of potassium permanganate. After cooling, the reaction mixture was suction-filtered through celite, and the desired product was precipitated by addition of concentrated hydrochloric acid. Rf -value (benzene/acetone = 3/1): 0.2-0.4.

Workup

  1. temperaturethe solution was heated at its boiling point for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was suction-filtered through celite
  4. customthe desired product was precipitated by addition of concentrated hydrochloric acid

Sources & evidence

ORD record
ord-607d4c508e6e4f9fac3ed66c1e40bcb9
Source dataset
uspto-grants-1977_07
Patent number
US04038407

Reaction notes

Loading…