Syringaldehyde → HCID 6006953, compound

HRID 1504585Notes

Reaction equation

HRID 1504585 reaction equation
[CH:1](=O)[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[NH:14]1[CH2:20][C:18](=[O:19])[NH:17][C:15]1=[O:16].C([O-])(=O)C.[Na+]>C(O)(=O)C>[OH:8][C:7]1[C:9]([O:10][CH3:11])=[CH:12][C:2](/[CH:1]=[C:20]2/[C:18](=[O:19])[NH:17][C:15](=[O:16])[NH:14]/2)=[CH:3][C:4]=1[O:5][CH3:6]

Participants

5

Reactant 3

HCID 8655SyringaldehydeHCID 10006HydantoinHCID 517045Sodium Acetate

Product 1

HCID 6006953HCID 6006953, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In an acetic acid (1.6 mL) solvent, a suspension including syringaldehyde (300 mg, 1.65 mmol), hydantoin (198 mg, 1.98 mmol), and sodium acetate (405 mg, 4.94 mmol) was refluxed for 24 hours, and after cooling, the produced precipitate was filtered. The filtered solid was washed with methylene chloride and a small amount of water. After drying under reduced pressure, a target compound was obtained (192.9 mg, 44.3%).

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureafter cooling
  3. filtrationthe produced precipitate was filtered
  4. washThe filtered solid was washed with methylene chloride
  5. customAfter drying under reduced pressure
  6. customa target compound was obtained (192.9 mg, 44.3%)

Sources & evidence

ORD record
ord-57b8b10bd0354822b445d3d6ab62bc06
Source dataset
uspto-grants-2015_12
Patent number
US09216148B2

Reaction notes

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