89610-22-0Relevant articles and documents
Orthoamides, XL. - Preparation of 1,1,2,3,3-Pentasubstituted and 1,1,2,2,3,3-Hexasubstituted Guanidinium Salts and 1,1,2,3,3-Pentaalkylguanidines
Kantlehner, Willi,Haug, Erwin,Mergen, Walter W.,Speh, Peter,Maier, Thomas,et al.
, p. 108 - 126 (2007/10/02)
N,N,N',N'-(Tetramethyl)thiourea (1) reacts with N,N-dimethylcarbamoyl chloride (2) to give the guanidinium salt 3a.The carbenium salt 4, obtained from 1 and dimethyl sulfate, affords on treatment with dimethylamine the guanidinium salt 3b.Reaction of phosgene with N,N,N',N'-tetraalkylureas yields the chloroformamidinium chlorides 5 which are transformed by mixtures of primary or secondary amines and tertiary amines into mixtures of guanidinium salts and ammonium salts.From these mixtures, by means of sodium hydroxide, have been isolated the guanidinium salts 3a, 6, and 11, respectively.Some of the salts 3a and 6 are converted into the corresponding tetraphenylborates 7.The fluoroborates 8a and 8b are obtained from guanidinium chlorides 3a and 6h, respectively.By anion exchange in 8a, b the salts 9, 10 have been prepared.Alkylation of the guanidines 12 affords the guanidinium salts 13.
