Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate
American Journal of Heterocyclic Chemistry
Volume 5, Issue 1, March 2019, Pages: 4-6
Received: Jan. 25, 2019;
Accepted: Mar. 15, 2019;
Published: Apr. 8, 2019
Views 143 Downloads 60
Gunanka Hazarika, Department of Chemistry, North Eastern Regional Institute of Science and Technology, Nirjuli, Itanagar (Arunachal Pradesh), India
Pradeep K. Tripathy, Department of Chemistry, North Eastern Regional Institute of Science and Technology, Nirjuli, Itanagar (Arunachal Pradesh), India
Follow on us
The attraction of isothiocyanates as synthons and as cyclizing agents continues due to their diverse reactions and also due to their easy availability. It would not be out of place to mention that, in comparison to isocyanates (-N=C=O), their Sulphur analogues, isothiocyanates (-N=C=S), are less unpleasant and to some extent less hazardous. The use of isocyanates is drastically limited by the researchers  after December 3, 1984 which is the date of Bhopal Disaster held in Union carbide factory, Bhopal, Madhya Pradesh (India) due to the leakage of Methyl isocyanate (MIC) where thousands of people were died due to the toxic effect of MIC (Me-N=C=O). In the present study, a mixture of Phenyl isothiocyanate (2) and monocarboxylic acid (1), in the ratio of 1:1 and Phenyl isothiocyanate (2) and dicarboxylic acid (4) in the ratio of 2:1are taken for condensation reaction by heating at 160°-170°C for 15 minutesunder solvent free condition. Pyridine was used as a catalyst/ base in both the cases. The products obtained were monoanilides (3) and dianilides (5) of mono- and dicarboxylic acids respectively which were recrystallized from aqueous ethanol. Dicarboxylic acids gave unexpected results in some of the cases. For example, Phthalic acid produces N-phenylphthalimide irrespective of the molar ratio of the acid and Phenyl isothiocyanate whereas maleic acid produces neither mono- nor dianilides with Phenyl isothiocyanate under the present condition. A proper systematic investigation was carried out towards the condensation of Phenyl isothiocyanate with mono- and dicarboxylic acids.
Monocarboxylic Acids, Dicarboxylic Acids, Phenyl Isothiocyanate, Pyridineand Solvent Free
To cite this article
Pradeep K. Tripathy,
Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate, American Journal of Heterocyclic Chemistry.
Vol. 5, No. 1,
2019, pp. 4-6.
Copyright © 2019 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/
) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Sandler SR and Karo W, “Organic functional group preparations”, Ed. Blomquist AT, Academic Press, New York, 1963; 269.
Garcia J and Vilarrasa J, Tetrahedron Lett, 1982; 23: 1127-28.
Ram RN, AshareRam and Mukerjee AK, Chemistry and Industry (London) 1983; 569.
Ashare Ram, Ram RN and Mukerjee AK, Indian J. Chem. 1984; 23B: 759-60.
Vogel AIA ‘Textbook of Practical Organic Chemistry’, 5th Edition, Addison Wesley Longman Limited, UK, 1989.
Mukerjee AK and Ashare Ram, Chemical Reviews 1991; 91: 1-24.
‘CRC Handbook of Chemistry and Physics’, Edited by Lide David R., 88th Edition (2007-2008).
‘A Handbook of Organic Analysis: Qualitative and Quantitative’, Clarke HT, 4th Edition (1927), Published by Wiley International, London.
‘Practical Organic Chemistry’, Mann Frederick George and Saunders Bernard Charles, 4th Edition (1960), Published by Longman Inc., New York.
Drobnica L, Kristian P and Augustin J, ‘The Chemistry of cyanates and their thio-derivatives’ Part 2, Ed Patai S, New York, John Wiley and Sons, 1977;1003.