The reaction of imidazolidine-2-thione with carbon disulphide

Abstract

The reaction of imidazolidine-2-thione (ethylenethiourea) with carbon disulphide in the presence of strong bases was investigated. The use of sodium hydride as base afforded 1,2-bis-[(2-thioxoimidazolidin-1-yl)thiocarboxamido]ethane (6) and 2,3,6,7-tetrahydrodi-imidazo[2,1-b:1,2-e][1,3,5]thiadiazine-5-thione (8). On the other hand, reaction using n-butyl-lithium, followed by methylation, gave a dimethylated compound, methyl 2-methylthio-4,5-dihydroimidazole-1-carbodithioate (11).