Abstract
Abstract 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/POCl3 adduct is treated with the silylamine 15.
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