Comparison of the reactivities of 2-mercaptoaniline and 2-hydroxyaniline with 2-chloronicotinoyl chloride

Authors: De Souza, M.V.N.; Vasconcelos, T.R.A.; Wardell, S.M.S.V.; Wardell, J.L.; Carvalho, E.M.


Abstract

The reaction between equimolar 2-chloronicotinoyl chloride and 2-mercaptopyridine in ClCH2CH2Cl, after 30 minutes refluxing in ClCH2CH2Cl solution, produced pyrido[2,3,b][1,5]benzothiazepin-5(H)one 7, and 6-[3-(2-benzothiazolyl)pyridin-2-yl)thio]-N-[3-(2-benzothiazolyl)pyridin-2-yl]aniline 8. In contrast, the reaction using the same reaction conditions between equimolar 2-chloronico- tinoyl chloride and 2-hydroxypyridine, produced the simple amide, 2-chloro-N-(2-hydroxyphenyl) nicotinamide 9. 2-Chloro-N-(2-mercaptophenyl)nicotinamide was considered to be a common intermediate in the formation of 7 and 8. The characterizations of 7–9 were achieved by X-ray crystallography. The conformations of 7 and 8 in the solid state can be described as “U” and “V”-shaped, respectively.
Keywords: 2-Benzothiazolyl derivatives, 2-Chloronicotinoyl chloride, X-ray crystallography, Pyrido[2,3,b][1,5]benzothiazepin-5(H)one Document Type: Research Article DOI: http://dx.doi.org/10.1080/17415990600708627 Publication date: 22 de Agosto de 2006

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