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

HRID 1721031Notes

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 the above method, 2-(methylthio)benzamide is produced from 2-(methylthio)benzoylchloride; oxidized with periodic acid to 2-(methylsulfinyl)benzamide; and cyclized in the presence of thionyl chloride to yield a 1,2-benzisothiazol-3-one.

Sources & evidence

ORD record: ord-a2c83e31ab3c47f88457a16b9ff3579d
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05508416

Reaction notes

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