Carbon disulfide reaction with ethylene diamine

The reaction of the aminothienopyrimidine nitrile 46 with ethylene diamine and subsequent condensation with triethyl orthoformate, carbon disulfide, or aldehydes, yields partially reduced imidazo[l,2-c]pyrimido[5, 4 4,5]thieno[2,3-e]pyrimidines 47. Triazolo compounds 49 can be obtained from the hydrazino compounds 48 <97PHA500 97CA(127)205545>. 

The reaction of ethylene diamine, carbon disulfide and dilute sodium hydroxide in a aqueous medium afforded disodium ethylenebis-dithiocarbamate, known by the tradename Nabam (8-11), and the treatment of the salt with zinc chloride furnished zinc ethyleneblsdithio-carbamate, known by the tradename Zlneb (10, 12, 13). 

The reaction of carbon disulfide with 1,2-alkylene diamines (I) yields N-(2-aminoethyl) dithiocarbamic acids (II) which split off hydrogen sulfide thermally to give imidazolidine-2-thiones (III) (Hofmann-process). The simplest example, the reaction of carbon disulfide with ethylenediamine, is described in Organic Synthesis (5). The reaction is general for N,N -dialkyl-, N,N -diaryI, as well as for N,N -bis-(arylakyl) ethylene diamines. The rate of reaction is determined by the basicity of the diamine. Electron-donor substituents in the para-position of N-aromatically substituted ethylene diamines accelerate dithiocarbamate formation electron-acceptor groups retard it. 

The members of the second subgroup are prepared from ethylene diamine (20) or its derivatives by reaction with carbon disulfide. In a sodium hydroxyde medium the disodium salt nabam, in an ammonium hydroxide medium, the diammonium salt amobam is formed (21). The sodium-ammonium salt, nambam, can also be prepared. These active substances are soluble in water. They cannot be used as foliage fungicides because of their phytotoxicity. On the other hand, they can be applied with good results for seed treatment. These compounds are intermediate products of the water-insoluble metal salts of N,N-ethylene-bisdithiocarbamic acid. c... 

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