Diethylamine → HCID 21586166, compound

HRID 1163873Notes

Reaction equation

HRID 1163873 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[N:24]1C(=O)C(=CC2C=CC=CC=2)S[C:25]1=[S:37])(=O)C.[CH2:38]([NH:40][CH2:41][CH3:42])[CH3:39]>CO>[C@@H:6]1([NH:24][C:25]([N:40]([CH2:41][CH3:42])[CH2:38][CH3:39])=[S:37])[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 54028629HCID 54028629, compound

Product 1

HCID 21586166HCID 21586166, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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 diethylamine (1.76 g., 0.024 mole) in 50 ml. of methanol in a pressure bottle. The reaction mixture was stirred at room temperature for 21 hours in the pressure bottle with the stopper well closed. The mixture was filtered and the filtrate was evaporated to a brownish syrupy material below 30° in vacuo. The residue 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 residual solid was dried at room temperature in vacuo. The solid was partially dissolved in ethyl acetate to give a slurry, and chromatographed on a column of silica gel (1×20 cm) using ethyl acetate as the first solvent (60 ml.) and acetone as the second solvent (100 ml.). The 100 ml. of acetone effluent was reduced to ca. 25 ml. and was set aside at room temperature. The beige crystalls were filtered, washed with acetone, and dried at room temperature in vacuo, yielding 0.51 g. (81.5%); m.p. 106°-109°(dec.)

Workup

  1. customwell closed
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to a brownish syrupy material below 30° in vacuo
  4. dissolutionThe residue 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. customthe residual solid was dried at room temperature in vacuo
  9. dissolutionThe solid was partially dissolved in ethyl acetate
  10. customto give a slurry
  11. customchromatographed on a column of silica gel (1×20 cm)
  12. customwas set aside at room temperature
  13. filtrationThe beige crystalls were filtered
  14. washwashed with acetone
  15. customdried at room temperature in vacuo
  16. customyielding 0.51 g

Sources & evidence

ORD record
ord-ae4800b5506047f48c6dd9573651d151
Source dataset
uspto-grants-1983_01
Patent number
US04367226

Reaction notes

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