Efficient conversion of substituted aryl thioureas to 2-aminobenzothiazoles using benzyltrimethylammonium tribromide.
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 by excess reagent. We have developed a direct procedure from isothiocyanates and amines using tetrabutylammonium thiocyanate (Bu4NSCN) and PhCH2NMe3Br3 to afford functionalized 2-aminobenzothiazoles.
Jordan
Alfonzo D
AD
Drug Discovery Division, Johnson & Johnson Pharmaceutical Research and Development, P.O. Box 0776, Welsh and McKean Roads, Spring House, Pennsylvania 19477-0776, USA. ajordan@prdus.jnj.com
Luo
Chi
C
Reitz
Allen B
AB