Orthoamides LXVIII1: N,N’,N’’-Peralkylated Guanidinium Salts by Alkylation of N,N,N’,N’,N’’-Pentasubstituted Guanidines

Willi Kantlehner,1,2* Kai Edelmann,1 Alexander Gissel,1 Oliver Scherr,1 Jens Vetter,1 Markus Wezstein,1 Georg Ziegler,1 J. Mezger,1 and Boyan Iliev1,2

1 Hochschule Aalen, Fakultät Chemie/Organische Chemie, Beethovenstr. 1, D-73430 Aalen
2 Universität Stuttgart, Institut für Organische Chemie, Pfaffenwaldring 55, D-70569 Stuttgart
* Corresponding author: E-mail: willi.kantlehner@htw-aalen.de

Starting from secondary amines and N,N-dialkylcarbamoylchlorides or phosgene N,N’-peralkylated ureas 2b, d-k have been prepared, which were converted by phosgene to the not isolated chloroformamidinium chlorides 3. From these N,N,N’,N’,N’’-pentasubstituted guanidines 5 could be obtained by treatment with primary amines/triethylamine and sodium hydroxide. The alkylation of the guanidines which methyl- and ethyl iodide afforded the guanidinium iodides 7a-q. Two of them (7m, g) are room temperature ionic liquids (RTIL) (mp. < 25 °C) and another five compounds (7c, f, h, i, p) are ionic liquids (mp < 100 °C).

Keywords: N,N’,N’’-Peralkylated guanidinium salts, N,N’,N’’-Peralkylated guanidines, ureas, alkylation, ionic liquids