Synthesis 2015; 47(20): 3186-3190
DOI: 10.1055/s-0034-1381024
paper
© Georg Thieme Verlag Stuttgart · New York

tert-Butyl Hypochlorite Mediated Oxidative Chlorination of S-Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides

Kui Qiu*
a   School of Chemistry and Chemical Engineering, Chongqing University of Science and Technology, Chongqing 401331, P. R. of China   Email: qiucqust@163.com
,
Rennan Wang
b   China Petroleum Daqing Petrochemical Co. Refinery, Daqing 163000, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 03 February 2015

Accepted after revision: 13 May 2015

Publication Date:
17 July 2015 (online)


Abstract

Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.