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N , N , N ′, N ′, N ″, N ″-Hexamethylguanidinium chloride  9c  was prepared by treating the reaction mixture formed from  N , N , N ′, N ′-tetramethylurea ( 1a ) and phthaloyl chloride ( 16 ) with dimethyltrimethylsilylamine  15 .  N , N , N ′, N ′-Tetramethyl-chloroformamidinium chloride ( 2a ) is an intermediate in this synthesis. The chloroformamidinium chloride  2a  can also be prepared by treating the urea  1a  with thionyl chloride or phosphorus pentachloride, respectively. The guanidinium salt  9c  can be obtained from the crude  2a  thus prepared and the silylamine  15 . From urea/phosphoryl chloride adducts and primary aromatic amines have been prepared guanidines  38 , which are converted to  N , N ′-diaryl- N , N ′, N ″, N ″-tetramethyl-guanidinium iodides  39  on treatment with methyl iodide. The  N , N ′, N ″-trimethyl- N , N ′, N ″-triphenylguanidinium salt  44a  was prepared from the chloroformamidinium salt  43  and  N -methylaniline. The guanidinium salt  9c  is the reaction product when the urea  1a /POCl 3  adduct is treated with the silylamine  15 .

zeitschrift für naturforschung b

Orthoamide und Iminiumsalze, LXXXVIII. Synthese  N,N,N ′ ,N ′ ,N ″ ,N ″ - persubstituierter Guanidiniumsalze aus  N,N ′ - persubstituierten Harnstoff/Säurechlorid-Addukten**