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Note | Regular issue | Vol 53, No. 12, 2000, pp.2803-2808
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9046
Sythesis of 2-(2-Alkoxycarbonylphenylthio)-1,2-benzisothiazolin-3-ones from 2-Sulfenamoylbenzoates

Masao Shimizu,* Toshiyuki Takagi, Motonari Shibakami, Yasuo Gama, and Isao Shibuya

*National Institute of Material and Chemical Research, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan


The Mechanism of formation of 2-(2-alkoxycarbonylphenylthio)-1,2-benzisothiazolin-3-ones, which were obtained by the heating of 2-sulfenamoylbenzoates, was investigated. It appears that transamination occurred on the sulfur atom of a 2-sulfenamoylbenzoate between the amino group and the 1,2-benzisothiazolin-3-one, which formed by the cyclization of methyl 2-sulfenamoylbenzoate after heating, to give 2-(2-methoxycarbonylphenylthio)-1,2-benzisothiazolin-3-ones. Several types of 2-sulfenyl-1,2-benzisothiazolin-3-ones were synthesized from the 2-sulfenamoylbenzoates.