Water → 7-Chloro-1,2-benzisothiazole-1,1-dioxide

HRID 1709093Notes

Reaction equation

HRID 1709093 reaction equation
C([N:5]1[CH:9](O)[C:8]2[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[C:7]=2[S:6]1(=[O:17])=[O:16])(C)(C)C.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[Cl:15][C:14]1[C:7]2[S:6](=[O:17])(=[O:16])[N:5]=[CH:9][C:8]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13686308HCID 13686308, compound

Product 1

HCID 136863097-Chloro-1,2-benzisothiazole-1,1-dioxideYield 69.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 37 g of 2-t-butyl-3-hydroxy-7-chloro-2,3-dihydro-1,2-benzoisothiazole-1,1-dioxide and 0.2 g of tosic acid in 370 mls of benzene was refluxed through a Dean-Stark water separator for 16 hours, cooled in ice and filtered to give 18.9 g of the title compound as colorless crystals, m.p. 162°-164° C.

Workup

  1. temperaturecooled in ice
  2. filtrationfiltered

Sources & evidence

ORD record
ord-7182f13f08984175b00f21292b7204c2
Source dataset
uspto-grants-1990_08
Patent number
US04948416

Reaction notes

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