The Journal of organic chemistry

Efficient conversion of substituted aryl thioureas to 2-aminobenzothiazoles using benzyltrimethylammonium tribromide

AD Jordan, C Luo, AB Reitz

文献索引：Jordan, Alfonzo D.; Luo, Chi; Reitz, Allen B. Journal of Organic Chemistry, 2003 , vol. 68, # 22 p. 8693 - 8696

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被引用次数: 110

摘要

The reaction of molecular bromine (Br2) with arylthioureas is known to produce 2- aminobenzothiazoles (Hugerschoff reaction). We show here that benzyltrimethylammonium tribromide (1, PhCH2NMe3Br3), a stable, crystalline organic ammonium tribromide (OATB), can be readily utilized as an alternative electrophilic bromine source. It is easier to control the stoichiometry of addition with an OATB, which minimizes aromatic bromination caused ...