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A simple and efficient synthesis of N-[3-chloro-4-(4-chlorophenoxy)-phenyl]-2-hydroxy-3,5-diiodobenzamide, rafoxanide

A method for the synthesis of rafoxanide 6, a halogenated salicylanilide used as an efficient anthelmintic in sheep and cattle, is presented. Rafoxanide 6 was synthesized in only three steps from readily available 4-chlorophenol with 74% overall yield. The synthesis has two key stages: the first was...

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Autores principales: Kesternich, Víctor, Pérez-Fehrmann, Marcia, Quezada, Víctor, Castroagudín, Mariña, Nelson, Ronald, Martínez, Rolando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Versita 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10176281/
https://www.ncbi.nlm.nih.gov/pubmed/37362790
http://dx.doi.org/10.1007/s11696-023-02846-9
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author Kesternich, Víctor
Pérez-Fehrmann, Marcia
Quezada, Víctor
Castroagudín, Mariña
Nelson, Ronald
Martínez, Rolando
author_facet Kesternich, Víctor
Pérez-Fehrmann, Marcia
Quezada, Víctor
Castroagudín, Mariña
Nelson, Ronald
Martínez, Rolando
author_sort Kesternich, Víctor
collection PubMed
description A method for the synthesis of rafoxanide 6, a halogenated salicylanilide used as an efficient anthelmintic in sheep and cattle, is presented. Rafoxanide 6 was synthesized in only three steps from readily available 4-chlorophenol with 74% overall yield. The synthesis has two key stages: the first was salicylic acid iodination, adding iodine in the presence of hydrogen peroxide, which allowed obtaining a 95% yield. The second key stage was the reaction of 3,5-diiodosalicylic acid 5 with aminoether 4, where salicylic acid chloride was formed in situ with PCl(3) achieving 82% yield. Chemical characterization of both intermediates and final product was achieved through physical and spectroscopic (IR, NMR and MS) techniques. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11696-023-02846-9.
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spelling pubmed-101762812023-05-14 A simple and efficient synthesis of N-[3-chloro-4-(4-chlorophenoxy)-phenyl]-2-hydroxy-3,5-diiodobenzamide, rafoxanide Kesternich, Víctor Pérez-Fehrmann, Marcia Quezada, Víctor Castroagudín, Mariña Nelson, Ronald Martínez, Rolando Chem Zvesti Original Paper A method for the synthesis of rafoxanide 6, a halogenated salicylanilide used as an efficient anthelmintic in sheep and cattle, is presented. Rafoxanide 6 was synthesized in only three steps from readily available 4-chlorophenol with 74% overall yield. The synthesis has two key stages: the first was salicylic acid iodination, adding iodine in the presence of hydrogen peroxide, which allowed obtaining a 95% yield. The second key stage was the reaction of 3,5-diiodosalicylic acid 5 with aminoether 4, where salicylic acid chloride was formed in situ with PCl(3) achieving 82% yield. Chemical characterization of both intermediates and final product was achieved through physical and spectroscopic (IR, NMR and MS) techniques. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11696-023-02846-9. Versita 2023-05-12 /pmc/articles/PMC10176281/ /pubmed/37362790 http://dx.doi.org/10.1007/s11696-023-02846-9 Text en © Institute of Chemistry, Slovak Academy of Sciences 2023, Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.
spellingShingle Original Paper
Kesternich, Víctor
Pérez-Fehrmann, Marcia
Quezada, Víctor
Castroagudín, Mariña
Nelson, Ronald
Martínez, Rolando
A simple and efficient synthesis of N-[3-chloro-4-(4-chlorophenoxy)-phenyl]-2-hydroxy-3,5-diiodobenzamide, rafoxanide
title A simple and efficient synthesis of N-[3-chloro-4-(4-chlorophenoxy)-phenyl]-2-hydroxy-3,5-diiodobenzamide, rafoxanide
title_full A simple and efficient synthesis of N-[3-chloro-4-(4-chlorophenoxy)-phenyl]-2-hydroxy-3,5-diiodobenzamide, rafoxanide
title_fullStr A simple and efficient synthesis of N-[3-chloro-4-(4-chlorophenoxy)-phenyl]-2-hydroxy-3,5-diiodobenzamide, rafoxanide
title_full_unstemmed A simple and efficient synthesis of N-[3-chloro-4-(4-chlorophenoxy)-phenyl]-2-hydroxy-3,5-diiodobenzamide, rafoxanide
title_short A simple and efficient synthesis of N-[3-chloro-4-(4-chlorophenoxy)-phenyl]-2-hydroxy-3,5-diiodobenzamide, rafoxanide
title_sort simple and efficient synthesis of n-[3-chloro-4-(4-chlorophenoxy)-phenyl]-2-hydroxy-3,5-diiodobenzamide, rafoxanide
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10176281/
https://www.ncbi.nlm.nih.gov/pubmed/37362790
http://dx.doi.org/10.1007/s11696-023-02846-9
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