Reactions of aniline in acetic acid solutions containing cyanuric chloride and hydrogen chloride acceptors

Canadian Journal of Chemistry

Volumn 85, Issue 12, 2007, Pages 1070-1074

  Kolmakov, Kirill A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Acetic acid; Acylation; Aniline; Aryl amination; Cyanuric chloride

Indexed keywords

ACETIC ACID; ACYLATION; CHLORINE COMPOUNDS; REACTION KINETICS;

ARYL AMINATION; CYANURIC CHLORIDE; HYDROGEN CHLORIDE;

ANILINE;

EID: 38849128839     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V07-129     Document Type: Article

References (16)

1. For the reactions and properties of cynauric chloride and cyanuric acid, see: (a) E.M. Smolin and L. Rapoport. In The chemistry of heterocyclic compounds. Interscience Publishers, NY. 1959. p. 53;
2. (b) J.T. Thurston, J.R. Dudley, D.W. Kaiser, I. Hechenbleikner, F.C. Schaefer, and D. Holm-Hansen. J. Am. Chem. Soc. 73, 2981 (1951);
3. (c) W.M. Pearlman and C.K. Banks. J. Am. Chem. Soc. 70, 3726 (1948);
4. (d) S. Horrobin. J. Chem. Soc. Chem. Commun. 4130 (1963);
5. (e) K. Tagaki, T. Hattori, H. Kunisada, and Y. Yuki. J. Polym, Sci., Part A: Polym. Chem. 38, 4385 (2000).
6. For an efficient "green" approach to aryl animation of cyanuric chloride using acetic acid as solvent, see: K.A. Kolmakov. J. Heterocycl. Chem. In press.
7. For the acylation of amines in acetic acid medium, see: (a) K.V Krishna Mohan, N. Narender, and S.J. Kulkarni. Green Chem. 8, 368 (2006);
8. (b) V.G. Shabalin, M.M. Chemeris, and V.V. Kon'shin. Izv. Vyssh. Uchebn. Zaved. Lesn. Zh. 1, 81 (2004);
9. (c) L.M. Litvinenko, D.M. Aleksandrova, and S.F. Prokopovich. Ukr. Khim. Zh. 27, 494 (1961);
10. (d) for the interaction between acid chlorides and triethylamine see: J. Kajima Mulengi, O. Bensaid, and S. Bensalem. J. Soc. Alger. Chim. 6, 207 (1996).
11. Cyanuric chloride, a reagent for the preparation of acid chlorides, amides, and esters, see: R.J. Lahoti and D.R. Wagle. Indian J. Chem. Sect. B, 20, 852 (1981).
12. Activated ester method in peptide synthesis, see: N.L. Benoiton. Chemistry of peptide synthesis. CRC Press. 2005. p. 36.
13. Acetic acid solutions of electrolytes, see: S. Bruckenstein and I.M. Kolthoff. J. Am. Chem. Soc. 78, 2974 (1956) and the refs. cited therein.
14. E. Kolehmainen, K. Laihia, R. Kauppinen, D. Rasola, and A. Puchala. J. Phys. Org. Chem. 8, 577 (1995).
15. For chromatographic analysis of acid chlorides and anhydrides see: (a) J.M. Bissinger, K.T. Rullo, T.J. Stoklosa, C.M. Shearer, and N.J. De Angelis. J. Chromatogr. 268, 102 (1983);
16. (b) P. Maki-Arvela, E. Paatero, and T. Salmi. J. Chem. Technol. Biotechnol. 61, 1 (1994).