Benzylamine → HCID 54275063, 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 benzylamine (2.58 g., 0.024 mole) in 50 ml. of methanol in a pressure bottle. The reaction mixture was stirred at room temperature for 23 hours in the pressure bottle with the stopper well closed. The mixture was filtered, and the filtrate was evaporated to a sticky syrup below 30° in vacuo. The residual syrup was dissolved in the minimum ammount of acetone, and anhydrous ether was added to the solution to give a yellow sticky solid. The supernatant was decanted, and the residual sticky solid was dissolved in the minimum amount of acetone. Benzene was added to the solution to give a precipitate. The 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 and acetone as the second solvent. Fifty ml. of ethyl acetate effluent was collected in the first Erlenmeyer flask and 75 ml. of acetone effluent was collected in the second Erlenmeyer flask. The volume of the acetone effluent was reduced ca. 25 ml. and was set aside at 5° for 16 hours. The white precipitate was filtered, washed with acetone, and dried at room temperature in vacuo, yielding 0.99 g. (64.2%); m.p. 97°-100° (dec.).

Provenance & Evidence