4-Methoxybenzylamine → HCID 22822371, compound

Participants

Reaction Steps

N-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-5-benzylidenerhodanine(1.102 g., 0.002 mole) was added to a solution of p-methoxybenzylamine(3.5 g., 0.024 mole) in 50 ml. of methanol in a pressure bottle. The reaction mixture was stirred for 19 hours at room temperature in the pressure bottle with the stopper well closed. The mixture was filtered and the filtrate was evaporated to a sticky syrup in vacuo. The residual syrup was dissolved in the minimum amount of acetone, and anhydrous ether was added to the solution to give a sticky yellow solid. The supernatent was decanted, and the residual sticky solid was dissolved in the minimum amount of actone. Ethyl acetate was added to the solution to give a precipitate. The solid 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 actone effluent was collected in the second Erlenmeyer flask. The volume of the acetone effluent was reduced to ca. 25 ml. and was set aside at 5° for 24 hours. The straw crystals were filtered, washed with ethyl acetate, and dried in vacuo at room temperature, yielding 0.525 g. (73.2%); m.p. 83°-85°(dec.).

Provenance & Evidence