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Paper | Regular issue | Vol 60, No. 8, 2003, pp.1855-1864
Published online, 15th July, 2003
DOI: 10.3987/COM-03-9809
Synthesis of 1,2-Benzisothiazolin-3-one by Transamination of Sulfenamides

Masao Shimizu,* Ayanobu Takeda, Hidenori Fukazawa, Yoshimoto Abe, and Isao Shibuya

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


N-Substituted sulfenamoylbenzoates were synthesized by transamination of N-unsubstituted sulfenamoylbenzoates with amines. The reaction did not always proceed by simple amine exchange between the amines and ammonia on the sulfur atom of the sulfenamides. In reactions with aliphatic amines, the sulfenamides cyclized to form N-substituted 1,2-benzisothiazolin-3-ones. The synthesis of 1,2-benzisothiazolin-3-ones by intramolecular transamination was also investigated by S-amination of 2-mercaptobenzamides.