Allylamine → HCID 54301797, compound

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.).

1. customwell closed
2. filtrationThe reaction mixture was filtered
3. customthe filtrate was evaporated to a syrupy material
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 solid
7. customThe supernatant was decanted
8. dissolutionthe residue was dissolved in the minimum amount of acetone
9. additionBenzene was added to the solution
10. customto give a precipitate
11. filtrationThe white precipitate was filtered
12. dissolutionpartially dissolved in ethyl acetate
13. customchromatographed on a column of silica gel(1×20 cm)
14. waitand was set aside at 5° overnight
15. customNo precipitate was formed
16. customThe solution was evaporated to dryness below 30° in vacuo
17. customThe formed solid was recrystallized from acetone
18. customto give a white precipitate
19. filtrationThe precipitate was filtered
20. washwashed with acetone
21. customdried at room temperature in vacuo
22. customyielding 0.591 g

ORD record

ord-caf4de2aced94f96849e7d7d593d6d97

Source dataset

uspto-grants-1983_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04367226