69082-76-4Relevant 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.
Reaction of Guanidinium Salts with Alkyl Bromides and Acid Chlorides
Kantlehner, Willi,Kapassakalidis, Johannis J.,Speh, Peter,Braeuner, Hans-Juergen
, p. 389 - 393 (2007/10/02)
The guanidinium salt 1a reacts with alkyl bromides 2a-g and acid chlorides 2h-k to give the nitriles 3a-g and the acyl cyanides 3h-k, respectively.Acyl isocyanates 4a,b have been obtained from the guanidinium cyanate 1d and the acid chlorides 2h,l.Reaction of the alkyl bromides 2b,c,m,n and acid chlorides 2h,l with the guanidinium thiocyanate 1e affords alkyl thiocyanates 5a-d and acyl isothiocyanates 6a,b, respectively.
