Chlorine → 1,2-Benzisothiazol-3(2H)-one

HRID 1781615

Reaction equation

HRID 1781615 reaction equation
C[S:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH:5]=[N:6]O.ClCl.S(Cl)(Cl)(=O)=[O:15]>ClC1C=CC=CC=1>[S:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=2[C:5](=[O:15])[NH:6]1

Participants

5

Reactant 3

HCID 24526ChlorineHCID 24648Sulfuryl chlorideHCID 7867572-(Methylthio)benzaldehyde oxime2×

Product 1

HCID 175201,2-Benzisothiazol-3(2H)-oneYield 91.1%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

From the monochlorobenzene layer obtained by the same procedures as in Example 1, 2-(methylthio)benzaldehyde oxime was isolated in the same manner as in Example 2. 39.7 g of the oxime isolated was dissolved in 150 g of monochlorobenzene. Then, the oxime was cyclized in the same manner as in Example 1 except that chlorine was changed to 35.3 g (0.26 mol) of sulfuryl chloride. As a result, 32.7 g of 1,2-benzisothiazol-3-one was obtained. The yield against 2-(methylthio)benzaldehyde oxime was 91%.

Sources & evidence

ORD record
ord-8e36c12d6bee48f7b869e675e19ea709
Source dataset
uspto-grants-1997_05
Patent number
US05633384

Linked notes

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