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

AD Jordan, C Luo, AB Reitz

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

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Citation Number: 110

Abstract

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 ...