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Journal of Chemical Sciences

, Volume 125, Issue 3, pp 607–613 | Cite as

Efficient acetylation of primary amines and amino acids in environmentally benign brine solution using acetyl chloride

  • KAUSHIK BASU
  • SUCHANDRA CHAKRABORTY
  • ACHINTYA KUMAR SARKAR
  • CHANDAN SAHAEmail author
Article

Abstract

Acetyl chloride is one of the most commonly available and cheap acylating agent but its high reactivity and concomitant instability in water precludes its use to carry out acetylation in aqueous medium. The present methodology illustrates the efficient acetylation of primary amines and amino acids in brine solution by means of acetyl chloride under weakly basic condition in the presence of sodium acetate and/or triethyl amine followed by trituration with aqueous saturated bicarbonate solution. This effort represents the first efficient use of this most reactive but cheap acetylating agent to acetylate amines in excellent yields in aqueous medium. This is a potentially useful green chemical transformation where reaction takes place in environment-friendly brine solution leading to easy work-up and isolation of the amide derivatives. Mechanistic rationale of this methodology is also important.

Graphical Abstract

Aromatic and aliphatic primary amines and amino acids have been acetylated efficiently in brine solution with acetyl chloride under weakly basic conditions in the presence of sodium acetate and/or triethyl amine. The methodology demonstrates successful use of acetyl chloride as a substitute of acetic anhydride for the purpose of acetylation in aqueous medium.

Keywords

Amines acetyl chloride brine sodium acetate triethyl amine 

Notes

Acknowledgements

We thank Prof. Krishnangshu Roy, Director and Prof. Santanu Tripathi, Head of the Department of Clinical and Experimental Pharmacology, School of Tropical Medicine, Kolkata for their interest in the work. We also thank Dr. Gautam Chattopadhyay, Post-Graduate Department of Chemistry, Presidency College for insightful discussions. We thank the Council of Scientific and Industrial Research (CSIR), New Delhi, India for providing a Senior Research Fellowship (Grant No. 09/951(0001)/2008-EMR-I) to one of the authors (SC).

References

  1. 1.
    Greene T W and Wuts P G M 1999 Protective groups in organic synthesis, 3rd edn (New York: John Wiley and Sons Ltd.)CrossRefGoogle Scholar
  2. 2.
    Furniss B S, Hannaford A J, Smith P W G and Tatchell A R (eds) 2006 Vogel’s textbook of practical organic chemistry, 5th edn (London: Pearson Education)Google Scholar
  3. 3.
    Furniss B S, Hannaford A J, Rogers V, Smith P W G and Tatchell A R (eds) 1978 Vogel’s textbook of practical organic chemistry, 4th edn (London: ELBS/Longman) p. 684Google Scholar
  4. 4.
    Naik S, Bhattacharjya G, Kavala V R and Patel B K 2004 ARKIVOC 55Google Scholar
  5. 5.
    De S K 2004 Tetrahedron Lett. 45 2919CrossRefGoogle Scholar
  6. 6.
    Reddy T S, Narasimhulu M, Suryakiran N, Mahesh K C, Ashalatha K and Venkateswarlu Y 2006 Tetrahedron Lett. 47 6825CrossRefGoogle Scholar
  7. 7.
    Yadav J S, Narsaiah A V, Basak A K, Goud P R, Sreenu D and Nagaiah K 2006 J. Mol. Cat. A: Chemical 255 78CrossRefGoogle Scholar
  8. 8.
    Das B and Thirupathi P 2007 J. Mol. Cat. A: Chemical 269 12CrossRefGoogle Scholar
  9. 9.
    Heravi M M, Bakhtiari K, Javadi N M, Oskooie H A and Bamoharram F F 2007 Monatshefte für Chem. 138 445CrossRefGoogle Scholar
  10. 10.
    Prasad H S, Srinivasa G R and Gouda D C 2005 Synth. Commun. 35 1189CrossRefGoogle Scholar
  11. 11.
    Choudary B M, Bhaskar V, Lakshmi Kantam M, Rao K K and Raghavan K V 2001 Catal. Lett. 74 207CrossRefGoogle Scholar
  12. 12.
    (a) Bahmachari G, Laskar S and Sarkar S 2010 Ind. J. Chem. 49B 1274; (b) Krishna Mohan K V V, Narendar N and Kulkarni S J 2006 Green Chem. 8 368Google Scholar
  13. 13.
    Olson V R and Feldman H B 1937 J. Am. Chem. Soc. 59 2003CrossRefGoogle Scholar
  14. 14.
    Ghosh R, Maiti S and Chakraborty A 2005 Tetrahedron Lett. 46 147CrossRefGoogle Scholar
  15. 15.
    Pasha M A, Reddy M B M and Manjula K 2010 Eur. J. Chem. 1 385CrossRefGoogle Scholar
  16. 16.
    Choudhary V R and Dumbre D K 2011 Catal. Commun. 12 1351CrossRefGoogle Scholar
  17. 17.

Copyright information

© Indian Academy of Sciences 2013

Authors and Affiliations

  • KAUSHIK BASU
    • 1
  • SUCHANDRA CHAKRABORTY
    • 2
  • ACHINTYA KUMAR SARKAR
    • 3
  • CHANDAN SAHA
    • 2
    Email author
  1. 1.Department of ChemistrySt. Paul’s Cathedral Mission CollegeKolkataIndia
  2. 2.Department of Clinical and Experimental PharmacologySchool of Tropical MedicineKolkataIndia
  3. 3.Department of ChemistryPresidency CollegeKolkataIndia

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