Triethylamine → HCID 178512726, compound

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A mixture of 2-(2-guanidinothiazol-4-ylmethylthio)ethyl isothiocyanate hydrogen maleate (0.712 g), 4-(2-aminoethyl)imidazole dihydrochloride (histamine dihydrochloride) (0.404 g), triethylamine (0.808 g) and methanol (35 ml) was stirred at room temperature overnight. The mixture was purified by preparative thin layer chromatography on Merck 60 F-254 plates using as solvent ethyl acetate/ethanol/ammonia (s.g. 0.88) 6:1:1 v/v/v, eluting the band of RF 0.4 from the plates with ethanol. Evaporation of the filtered extract followed by treatment with maleic acid in acetone gave a white solid which was filtered off and washed with acetone followed by a little cold ethanol to give 1-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]-3-[2-(imidazol-4-yl)ethyl]thiourea dimaleate hemihydrate, m.p. 100° C. (decomp.).

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