Propargylamine → 1-Propargylguanidine sulfate

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Reaction Steps

To a vigorously stirred suspension of 50.11 g. (0.18 moles) of S-methylthiouronium sulfate in 100 ml. of water is added 20 g. (0.36 moles) of propargyl amine under a blanket of nitrogen. The reaction mixture is stirred at room temperature for 4 hours and then warmed slowly to reflux and refluxed for 2 hours. The heat is removed and the reaction mixture allowed to stir at room temperature for 2 days. The mixture is then heated to reflux, filtered and then evaporated to near dryness. The residual oil is triturated in isopropanol and the solid which separates is filtered and dried. This material is then resuspended in 1 l. of boiling methanol and water added dropwise until all of the solid dissolves. The solution is then cooled in an ice bath and the solid which separates is filtered, washed with methanol and dried to give 1-propargylguanidine sulfate (m.p. 200°-201° C.).

Provenance & Evidence