Journal of Organic Chemistry 2010-12-17

Nitrile functionalized methimazole-based ionic liquids.

Amal I Siriwardana, Angel A J Torriero, Juan M Reyna-González, Iko M Burgar, Noel F Dunlop, Alan M Bond, Glen B Deacon, Douglas R Macfarlane

Index: J. Org. Chem. 75(24) , 8376-82, (2010)

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Abstract

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, LiNTf(2), 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.