Abstract 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.

中文翻译：

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Orthoamide 和 Iminiumsalze，IIC。Darstellung von N-(ω-氨基烷基)-N,N',N',N",N"-全烷基胍和N-(ω-氨基烷基)-N',N',N",N"-四甲基胍

摘要 N,N,N',N'-四烷基氯甲脒氯化物 1a、b 与 ω-二甲氨基烷基胺 19、20 反应生成 N-(ω-二甲基氨基烷基)-胍盐 12、13 和 N-(ω-二甲基氨基烷基)-胍盐的混合物盐21、22。这些混合物在用氢氧化钠水溶液处理时转化为脲15、17和N-(ω-二甲氨基烷基)-胍23、25的混合物。N-(3-二甲基氨基丙基)-胍25a与硫酸二甲酯以1:1的摩尔比反应得到N-(3-二甲基氨基丙基)-N,N,N',N',N",N的混合物”-五甲基-胍盐29a和N-(3-二甲基氨丙基)-N,N',N',N”,N”-五甲基-胍-双(甲基硫酸盐)33a。硫酸二甲酯以2:1的摩尔比对胍23a、25a的作用提供双季盐32a、33a。烷基化试剂如碘甲烷，苄基溴、烯丙基溴和氯乙腈以 1:1 的摩尔比攻击 N-(2-二甲基氨基乙基)-N',N',N",N"-四乙基胍 (23b) 以 1:1 的摩尔比在二甲基氨基乙基基团上干净地攻击铵盐 30a-d . 作为强碱，胍 23b 在形成胍盐 21c 的情况下使 β-氯丙腈和氯丙酮脱氯化氢。与此相反，溴乙酸乙酯与 N-(2-二甲氨基乙基)胍 23b 的反应发生在胍基上，得到胍盐 28c。用硫酸二甲酯对氯化胍 21a、22a 进行甲基化，得到具有混合阴离子的双季盐 35b、36b。从杂环胍14、16和烷基化试剂苄基溴和溴乙酸乙酯可以得到杂环胍盐37a、b、39a、b。与氯甲酸乙酯的反应以类似方式进行，得到胍盐37c、39c。N-烷基-N,N,N',N'-四甲基-(3-脲基丙基)胍盐41a、b可由N',N',N",N"-四甲基-N''-制备(3-脲基丙基)胍17a和烷基化化合物硫酸二甲酯和苄基溴。以这种方式获得的几种化合物分别转化为相应的四苯基硼酸盐和双（四苯基硼酸盐）。