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Note | Regular issue | Vol 51, No. 12, 1999, pp.3005-3012
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8706
A Facile Synthesis of 1,2-Benzisothiazolin-3-ones from Thiosalicylates

Masao Shimizu,* Hisashi Kikumoto, Takeo Konakahara, Yasuo Gama, and Isao Shibuya

*National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan


Synthesis of 1,2-benzisothiazolin-3-ones by cyclization of 2-sulfenamoylbenzoates, which were prepared from amination of thiosalicylates by hydroxylamine-O-sulfonic acid, was examined. Although treatment of methyl 2-sulfenamoylbenzoate on heating gave unexpected 2-(2-methoxycarbonylphenylthio)-1,2-benzisothiazolin-3-one, the treatment with base at room temperature afforded the corresponding 1,2-benzisothiazolin-3-ones in good yields.