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N , N , N′ , N′ -Tetraalkylchlorformamidiniumchlorides  1a ,  b  react with  ω -dimethylaminoalkylamines  19 ,  20  to give mixtures of  N -( ω -dimethylammonioalkyl)-guanidinium salts  12 ,  13  and  N -( ω -dimethylaminoalkyl)-guanidinium salts  21 ,  22 . These mixtures are transformed to mixtures of the ureas  15 ,  17  and  N -( ω -dimethylaminoalkyl)-guanidines  23 ,  25  on treatment with aqueous sodium hydroxide. The reaction of  N -(3-dimethylammoniopropyl)-guanidin  25a  with dimethylsulfate in a molar ratio of 1:1 delivers a mixture of the  N -(3-dimethylaminopropyl)- N,N,N′,N′,N″,N″- pentamethyl-guanidinium salt  29a  and the  N -(3-dimethylammoniopropyl)- N,N′,N′,N″,N″- pentamethyl-guanidinium-bis (methylsulfate)  33a . The action of dimethylsulfate on the guanidines  23a ,  25a  in a molar ratio of 2:1 affords the bisquarternary salts  32a ,  33a . Alkylating reagents as methyliodide, benzylbromide, allylbromide and chloroacetonitrile attack  N -(2-dimethylaminoethyl)- N′,N′,N″,N″- tetraethylguanidine ( 23b ) in a molar ratio of 1:1 cleanly at the dimethylaminoethylgroup to give the ammonium salts  30a – d . As a strong base the guanidine  23b  dehydrochlorinates  β -Chlorpropionitrile and chloroacetone under formation of the guanidinium salt  21c . In contrast to this the reaction of ethyl bromoacetate with the  N -(2-dimethylaminoethyl)guanidine  23b  occurs at the guanidinogroup giving the guanidinium salt  28c . The methylation of the guanidinium chlorides  21a ,  22a  with dimethyl sulfate affords the bis-quaternary salts  35b ,  36b  with mixed anions. From the heterocyclic guanidines  14 ,  16  and the alkylating reagents benzylbromide and ethyl bromoacetate the heterocyclic guanidinium salts  37a ,  b ,  39a ,  b  can be obtained. The reactions with ethyl chloroformiate proceed in an analogous way giving the guanidinium salts  37c ,  39c . The  N -alkyl- N,N,N′,N′- tetramethyl-(3-ureidopropyl)guanidinium salts  41a ,  b  can be prepared from the  N′,N′,N″,N″- tetramethyl- N′′ -(3-ureidopropyl) guanidine  17a  and the alkylating compounds dimethyl sulfate and benzyl bromide. Several compounds obtained that way were transformed to the corresponding tetraphenyloborates and bis(tetraphenylborates), respectively.

zeitschrift für naturforschung b

Orthoamide und Iminiumsalze, IIC. Darstellung von  N -( ω -Ammonioalkyl)- N,N′,N′,N″,N″- peralkylierten Guanidiniumsalzen und  N -( ω -Aminoalkyl)- N′,N′,N″,N″- tetramethylguanidinen