Saccharin → 4-trifluoroacetoxy-1,2-benzisothiazol-3(2H)-one-1,1-dioxide

HRID 1248778Notes

Reaction equation

[OH:1][C:2]1[C:7]2[C:8](=[O:13])[NH:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.S1(=O)(=O)C2C=CC=CC=2C(=O)N1.[F:26][C:27]([F:32])([F:31])[C:28](O)=[O:29].FC(F)(F)S(O)(=O)=O>>[F:26][C:27]([F:32])([F:31])[C:28]([O:1][C:2]1[C:7]2[C:8](=[O:13])[NH:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:29]

Participants

Reactant 4

HCID 5143Saccharin

HCID 6422Trifluoroacetic acid

HCID 62406Trifluoromethanesulfonic acid

HCID 14865224-hydroxy-1H-1,2-benzisothiazole-1,1,3(2H)-trione

Product 1

HCID 543729804-trifluoroacetoxy-1,2-benzisothiazol-3(2H)-one-1,1-dioxide

Procedure

The specification describes a process for preparing 4-hydroxy-1,2-benzisothiazol-3(2H)-one-1,1-dioxide, a sweetener, from 1,2-benzisothiazol-3(2H)-one-1,1-dioxide by anodic oxidation in the presence of trifluoroacetic acid or trifluoromethanesulfonic acid and, optionally, in the presence of salts which increase the conductivity. The oxidation is effected in an anhydrous medium and the 4-trifluoroacetoxy-1,2-benzisothiazol-3(2H)-one-1,1-dioxide formed as an intermediate when, for example, trifluoroacetic acid is used is decomposed with water to obtain the desired end product.

Sources & evidence

ORD record: ord-aa6994a49181462785998d04c8f4aa4f
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04626325

Reaction notes

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