Method for producing 1,2-benzisothiazol-3-ones

Details Method for producing 1,2-benzisothiazol-3-ones Method for producing 1,2-benzisothiazol-3-ones

1996-09-18

1998-06-30

Morris, Patricia L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D27504

Patent

active

057736260

ABSTRACT:
A method for producing a 1,2-benzisothiazol-3-one, having the steps of carrying out a reaction of a 2-(alkylthio)benzaldehyde with a hydroxylamine to give a 2-(alkylthio)benzaldehyde oxime and carrying out a reaction of the 2-(alkylthio)benzaldehyde oxime with a halogenating agent; and a method for producing a 1,2-benzisothiazol-3-one, having the steps of carrying out a reaction of a 2-halobenzonitrile with an alkanethiol in a heterogeneous solvent system in the presence of a base to give a 2-(alkylthio)benzonitrile and carrying out a reaction of the 2-(alkylthio)benzonitrile with an halogenating agent in the presence of water.

REFERENCES:
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A.J. Lawson, `Thermal fission of hydroxylamine derivatives with neighbouring-group participation by thioether functions: preparation of 1,2-benzoisothiazoles`, vol. 12, 1982 pp. 357-367.
F. Becke, H. Hagen `Eine neue Synthese von 1.2-Benzoisothiazolen`, Ann. Chem., vol. 729, 1969, pp. 146-151.
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M.L. Carmellino et al `Antimicrobial activity of fluorinated 1,2-benzisothiazol-3(2H)-ones and 2,2'-dithiobis(benzamides)`, Eur.J.Med.Chem.Chim.Ther., vol. 29, No. 10, 1994, pp. 743-752.
Y. Uchida, S. Kozuka `The Thermal Decomposition of N,O-Diacyl-N-t-butylhydroxylamines. III. Novel Routes to 2-Substituted 1,2-Benzoisothiazol-3-(2H)-ones`, Bull. Chem. Soc. Jon., vol. 55, No. 4, 1982, pp. 1183-1187.
"An Improved Mehtod for the Preparation of 2-Substituted 1,2-Benzisothiazol-3(2H)-Ones. Novel Cyclization of N-Substituted 2-Carbamoylbenzenesulfenyl Bromides on Activated Basic Alumina," Kamigata et al., Organic Preparations and Procedures Int., 15(5), 315-319 (1983).
"The Thermal Decomposition of N,O-Diacyl-N-t-butylhydroxylamines. III Novel Routes to 2-Substituted 1,2-Benzisothiazol-3-(2H)-ones," Uchida et al., Bull. Chem. Soc. Jpn., 55, 1183-1187 (1982).
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