Thionyl Chloride → 1,2-Benzisothiazol-3(2H)-one

HRID 965404Notes

Reaction equation

I(O)(=O)(=O)=O.C[S:7]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12])=O.S(Cl)(Cl)=O>>[S:7]1[C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11](=[O:12])[NH:13]1

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 65185Metaperiodic acid

HCID 12242117HCID 12242117, compound

Product 1

HCID 175201,2-Benzisothiazol-3(2H)-one

Procedure

In this method, 2-(methylthio)benzamide is produced from 2-(methylthio)benzoyl chloride; oxidized with periodic acid to 2-(methylsulfinyl)benzamide; and cyclized in the presence of thionyl chloride to yield a 1,2-benzisothiazol-3-one. ##STR1## (B) Org. Prep. Proced. Int., 15, 315-319(1983)

Sources & evidence

ORD record: ord-3dc21b545d6c40f7bca2193a2c84fd84
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773626

Reaction notes

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