4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 178485068, compound

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Reaction Steps

A solution of cyanoimino-methylaminomethanesulfonic acid (DBU salt) (0.70 g) and 2-(5-methylimidazol-4-ylmethylthio)ethylamine (0.57 g) in ethanol (14 ml) was heated under reflux for 7 hrs. After removal of the solvent under a reduced pressure, the residue was purified by column chromatography on SiO2 [eluant: CH3CN-CH3OH (4:1)]. After concentration of the eluate under a reduced pressure, the residue was subjected to preparative thin layer chromatography [SiO2, CH3COOCH3 -CH3OH- 28% NH3 (aq) (10:1:1)] and then recrystallized from CH3OH-CH3CN to give N"-cyano-N-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine (0.18 g). Yield 32.4%, m.p. 140°-141° C.

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