Siriwardana, Amal I., Torriero, Angel. A. J., Reyna-Gonzälez, Juan M., Burgar, Iko M., Dunlop, Noel F., Bond, Alan M., Deacon, Glen B. and MacFarlane, Douglas R. 2010, Nitrile functionalized methimazole-based ionic liquids, Journal of organic chemistry, vol. 75, no. 24, pp. 8376-8382, doi: 10.1021/jo101449q.
The alkylation reaction of 2-mercapto-1-methylimidazole 1b with 2-chloroacetonitrile and 2-chloropropionitrile produced S-alkyl methimazole chlorides 2a and 2b which were subjected to anion metathesis with lithium bis(trifluoromethanesulfonyl)amide, LiNTf2, to afford nitrile functionalized methimazole-based room temperature ionic liquids 3a and 3b in 94% and 89% yields, respectively. Ionic liquids 3a and 3b have reasonably wide electrochemical windows. The efficient extraction of Ag+ from aqueous media into 3a and 3b is also reported.
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