Water → 4-hydroxy-1H-1,2-benzisothiazole-1,1,3(2H)-trione

HRID 1248780

Reaction equation

HRID 1248780 reaction equation
[S:1]1(=[O:12])(=[O:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[O:10])[NH:2]1.FC(F)(F)C([O-])=[O:16].[Na+].O>FC(F)(F)C(O)=O>[OH:16][C:9]1[C:4]2[C:3](=[O:10])[NH:2][S:1](=[O:11])(=[O:12])[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5143SaccharinHCID 517019Sodium Trifluoroacetate

Product 1

HCID 14865224-hydroxy-1H-1,2-benzisothiazole-1,1,3(2H)-trioneYield 61%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4.6 g (25 mmol) of 1,2-benzisothiazol-3(2H)-one-1,1-dioxide (Saccharin®) were dissolved in 30 ml of trifluoroacetic acid and mixed with 4 g of sodium trifluoroacetate. The solution was electrolysed analogously to Example 1. After a charge quantity of 0.4 Ah had been used up the solution was added to water. It was extracted with chloroform and worked up as in Example 1. In addition to 3.3 g of starting material, 0.92 g of 4-hydroxy-1,2-benzisothiazol-3(2H)-one-1,1-dioxide were obtained after recrystallisation from water. This corresponds to a yield of 61% based on the starting material reacted;

Workup

  1. extractionIt was extracted with chloroform
  2. additionIn addition to 3.3 g of starting material

Sources & evidence

ORD record
ord-2a16ac6880be4a4eb206566ad2b4e1c3
Source dataset
uspto-grants-1986_12
Patent number
US04626325

Linked notes

Loading…