Allylamine → HCID 54301797, compound

Participants

Reaction Steps

N-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-5-benzylidenerhodanine(2.204 g., 0.004 mole) was added to a solution of allylamine(2.74 g., 0.048 mole) in 50 ml. of methanol in a pressure bottle. The reaction mixture was stirred at room temperature for 24 hours in the pressure bottle with the stopper well closed. The reaction mixture was filtered and the filtrate was evaporated to a syrupy material. The residual syrup was dissolved in the minimum amount of acetone, and anhydrous ether was added to the solution to give a sticky solid. The supernatant was decanted and the residue was dissolved in the minimum amount of acetone. Benzene was added to the solution to give a precipitate. The white precipitate was filtered, partially dissolved in ethyl acetate, and then chromatographed on a column of silica gel(1×20 cm) using ethyl acetate as the first solvent(60 ml.), acetone-ethyl acetate(3:7) as the second solvent(50 ml.), and acetone as the third solvent(80 ml.). The third acetone effluent was reduced to ca.25 ml. and was set aside at 5° overnight. No precipitate was formed. The solution was evaporated to dryness below 30° in vacuo. The formed solid was recrystallized from acetone to give a white precipitate. The precipitate was filtered, washed with acetone, and dried at room temperature in vacuo, yielding 0.591 g. (43.9%); m.p. 95°-97°(dec.).

Provenance & Evidence