4-Methoxybenzylamine → HCID 22822371, compound

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.).

1. customwell closed
2. filtrationThe mixture was filtered
3. customthe filtrate was evaporated to a sticky syrup in vacuo
4. dissolutionThe residual syrup was dissolved in the minimum amount of acetone, and anhydrous ether
5. additionwas added to the solution
6. customto give a sticky yellow solid
7. customThe supernatent was decanted
8. dissolutionthe residual sticky solid was dissolved in the minimum amount of actone
9. additionEthyl acetate was added to the solution
10. customto give a precipitate
11. filtrationThe solid was filtered
12. dissolutionpartially dissolved in ethyl acetate
13. customchromatographed on a column of silica gel (1×20 cm)
14. customof ethyl acetate effluent was collected in the first Erlenmeyer flask, and 75 ml
15. customof actone effluent was collected in the second Erlenmeyer flask
16. waitand was set aside at 5° for 24 hours
17. filtrationThe straw crystals were filtered
18. washwashed with ethyl acetate
19. customdried in vacuo at room temperature
20. customyielding 0.525 g

ORD record

ord-824252bcde26487f80c79aa70ebdd447

Source dataset

uspto-grants-1983_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04367226