Benzylamine → HCID 54275063, 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 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.).

1. customwell closed
2. filtrationThe mixture was filtered
3. customthe filtrate was evaporated to a sticky syrup below 30° in vacuo
4. dissolutionThe residual syrup was dissolved in the minimum ammount of acetone, and anhydrous ether
5. additionwas added to the solution
6. customto give a yellow sticky solid
7. customThe supernatant was decanted
8. dissolutionthe residual sticky solid was dissolved in the minimum amount of acetone
9. additionBenzene was added to the solution
10. customto give a precipitate
11. filtrationThe precipitate 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 acetone effluent was collected in the second Erlenmeyer flask
16. waitand was set aside at 5° for 16 hours
17. filtrationThe white precipitate was filtered
18. washwashed with acetone
19. customdried at room temperature in vacuo
20. customyielding 0.99 g

ORD record

ord-03cfbb02b67c4040ac3589ba582fb230

Source dataset

uspto-grants-1983_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04367226