シアナミドジチオ炭酸エステルおよびその関連化合物に関する合成的研究 (第1報) : シアミド誘導体に関する研究第78報

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Dialkylester of cyanamide-dithiocarbonic acid (1) is easily prepared by reaction of cyanamide, carbondisulfide and alkylating agents in the presenc of alkali. (1) is extremely active toward nucleophilic reagents, since it has reactive thioimidoester and aminonitrile-group. In order to develope a new synthetic route for preparing high-nitrogen compounds, the reactivity of (1) and the reaction between (1) and amino compounds derived from cyanamide was investigated The chemical behavior of (1) in alkaline media was examined ; in an alcoholic solution it was converted to dicyano-O-alkyl-isourea salt and cyanamide-carbonic acid ester salt, and in an aqueous solution, cyanamide-thiocarbonic ester salt. (1) reacted with guanidine in an alcoholic solution to give diamino-alkoxy-s-triazine through ester exchanging reaction, whereas in an acetonic solution, N-cyano-N′-guanyl-S-alkyl-isothiourea was formed together with a small amount of diaminomercapto-s-triazine. (1) also reacted with cyanamide and with dicyandiamide to give dicyano-S-alkyl-isothiourea salt and dicyano-melamine salt, respectively. The above substitution reaction was also carried out with success using other cyanamide-carbonic esters.
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