Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate

Gunanka Hazarika; Pradeep K. Tripathy

doi:doi:10.11648/j.ajhc.20190501.12

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Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate

Gunanka Hazarika, Pradeep K. Tripathy

Published in American Journal of Heterocyclic Chemistry (Volume 5, Issue 1)

Received: 25 January 2019 Accepted: 15 March 2019 Published: 8 April 2019

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Abstract

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 [6] 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.

Published in	American Journal of Heterocyclic Chemistry (Volume 5, Issue 1)
DOI	10.11648/j.ajhc.20190501.12
Page(s)	4-6
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2019. Published by Science Publishing Group

Keywords

Monocarboxylic Acids, Dicarboxylic Acids, Phenyl Isothiocyanate, Pyridineand Solvent Free

References

[1]	Sandler SR and Karo W, “Organic functional group preparations”, Ed. Blomquist AT, Academic Press, New York, 1963; 269.
[2]	Garcia J and Vilarrasa J, Tetrahedron Lett, 1982; 23: 1127-28.
[3]	Ram RN, AshareRam and Mukerjee AK, Chemistry and Industry (London) 1983; 569.
[4]	Ashare Ram, Ram RN and Mukerjee AK, Indian J. Chem. 1984; 23B: 759-60.
[5]	Vogel AIA ‘Textbook of Practical Organic Chemistry’, 5^th Edition, Addison Wesley Longman Limited, UK, 1989.
[6]	Mukerjee AK and Ashare Ram, Chemical Reviews 1991; 91: 1-24.
[7]	‘CRC Handbook of Chemistry and Physics’, Edited by Lide David R., 88^th Edition (2007-2008).
[8]	‘A Handbook of Organic Analysis: Qualitative and Quantitative’, Clarke HT, 4^th Edition (1927), Published by Wiley International, London.
[9]	‘Practical Organic Chemistry’, Mann Frederick George and Saunders Bernard Charles, 4^th Edition (1960), Published by Longman Inc., New York.
[10]	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.

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APA Style

Gunanka Hazarika, Pradeep K. Tripathy. (2019). Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate. American Journal of Heterocyclic Chemistry, 5(1), 4-6. https://doi.org/10.11648/j.ajhc.20190501.12

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ACS Style

Gunanka Hazarika; Pradeep K. Tripathy. Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate. Am. J. Heterocycl. Chem. 2019, 5(1), 4-6. doi: 10.11648/j.ajhc.20190501.12

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AMA Style

Gunanka Hazarika, Pradeep K. Tripathy. Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate. Am J Heterocycl Chem. 2019;5(1):4-6. doi: 10.11648/j.ajhc.20190501.12

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@article{10.11648/j.ajhc.20190501.12,
  author = {Gunanka Hazarika and Pradeep K. Tripathy},
  title = {Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {5},
  number = {1},
  pages = {4-6},
  doi = {10.11648/j.ajhc.20190501.12},
  url = {https://doi.org/10.11648/j.ajhc.20190501.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20190501.12},
  abstract = {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 [6] 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.},
 year = {2019}
}

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TY  - JOUR
T1  - Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate
AU  - Gunanka Hazarika
AU  - Pradeep K. Tripathy
Y1  - 2019/04/08
PY  - 2019
N1  - https://doi.org/10.11648/j.ajhc.20190501.12
DO  - 10.11648/j.ajhc.20190501.12
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 4
EP  - 6
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20190501.12
AB  - 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 [6] 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.
VL  - 5
IS  - 1
ER  -

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Author Information

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

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APA Style

Gunanka Hazarika, Pradeep K. Tripathy. (2019). Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate. American Journal of Heterocyclic Chemistry, 5(1), 4-6. https://doi.org/10.11648/j.ajhc.20190501.12

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ACS Style

Gunanka Hazarika; Pradeep K. Tripathy. Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate. Am. J. Heterocycl. Chem. 2019, 5(1), 4-6. doi: 10.11648/j.ajhc.20190501.12

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AMA Style

Gunanka Hazarika, Pradeep K. Tripathy. Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate. Am J Heterocycl Chem. 2019;5(1):4-6. doi: 10.11648/j.ajhc.20190501.12

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@article{10.11648/j.ajhc.20190501.12,
  author = {Gunanka Hazarika and Pradeep K. Tripathy},
  title = {Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {5},
  number = {1},
  pages = {4-6},
  doi = {10.11648/j.ajhc.20190501.12},
  url = {https://doi.org/10.11648/j.ajhc.20190501.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20190501.12},
  abstract = {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 [6] 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.},
 year = {2019}
}

Copy | Download

TY  - JOUR
T1  - Solvent Free Quick Conversion of Mono - And Dicarboxylic Acids into Their Corresponding Anilides with Phenylisothiocyanate
AU  - Gunanka Hazarika
AU  - Pradeep K. Tripathy
Y1  - 2019/04/08
PY  - 2019
N1  - https://doi.org/10.11648/j.ajhc.20190501.12
DO  - 10.11648/j.ajhc.20190501.12
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 4
EP  - 6
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20190501.12
AB  - 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 [6] 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.
VL  - 5
IS  - 1
ER  -

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