In the last years, intensive research has transformed specific functionalized ionic liquids from
the curiosity they used to be to a new type of medium with interesting properties: they cannot
evaporate nor inflame, can be used at a large range of temperature, easily recycled and reused,
making them solvents or catalysts of choice for green chemistry and in drug development as well
[1]. The following properties were also targeted: 1) straightforward and easy preparation,
applicable on larger scale; 2) presence of functional groups that could lead to favorable
interactions with substrates. Solvent free reactions have been demonstrated to be an efficient
technique for various organic reactions instead of using harmful solvents. Moreover, we
therefore were interested in the introduction of carboxyl group free on such derivatives.
Previously, we reported that in the presence of Me- or CNCH2CH2- functional groups of
starting imidazoles 3a or 3b product of quaternization with monochloroacetic acid is an oily
fluid mixture 4a, 5a or 4b, 5b as well [2].
In our efforts to investigate the range of organic reactions we report, herein, a simple, mild,
efficient, and practical method for the synthesis and easy separation of new vinylimidazolium
salts. The reaction of N-vinylimidazole 3c with monochloroacetic acid was examined according
to the scheme.

It was observed that unlike 3a,b two phase substance is formed during the mixing of
equimolar quantities of imidazole 3c with monochloroacetic acid at room temperature without
any solvent. It was found that compounds 4c, 5c can be easily separated each from one another
by decantation and whose composition and structure are confirmed by elemental analysis, IR and
NMR spectra. Finally, it is necessary to mention the kinetic resolution of 5a from 4a up to 98%.
It was hoped that this manipulation would result in a different catalytic properties of new
imidazolium salts and data will be presented in other communication.
The author gratefully acknowledges the bilateral MD-UC project (Ref. № 14.820.18.02.06/U)
for financial support and Prof. Macaev F. and Dr. Stîngaci E. for helpful discussions.
References:
1. Macaev F. Green chemistry protocols: specific ionic liquids as recyclable reagents, catalysts,
solvents and extractors. In «Environmental Security Assessment and Management of Obsolete
Pesticides in Southeast Europe», Eds. Simeonov L., Macaev F. Simeonova B., SPRINGER
Science+Business media B.V. 2013, p. 313-331.
2. Makaev F., Styngach E., Muntyanu V., Pogrebnoi S., Rybkovskaya Z., Barba A. Russ. J.Org.
Chem. 2007, 43, 1512.