Vanillin → HCID 59088090, compound

HRID 656302Notes

Reaction equation

HRID 656302 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][C:4]=1[OH:11].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:20]([N:28]=[C:29]=[S:30])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO.[Pt]>[CH2:12]([N:19]([CH2:9][C:7]1[CH:6]=[CH:5][C:4]([OH:11])=[C:3]([O:2][CH3:1])[CH:8]=1)[C:29]([NH:28][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[S:30])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1183VanillinHCID 7504BenzylamineHCID 16741Phenethyl Isothiocyanate

Product 1

HCID 59088090HCID 59088090, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Vaniline (200 mg) and benzylamine (129 mg) were dissolved in methanol (3 ml) and the solution was stirred for 30 minutes. To the solution was added a catalytic amount of 10% platinum/carbon to be subjected to the hydrogenation reaction (1 atm). After the completion of the reaction, the resulting mixture was filtered and evaporated under reduced pressure to remove methanol. The obtained residue was dissolved in dichloromethane (3 ml) and to the solution was added phenethylisothiocyanate (196 mg, 1.2 mmol), followed by stirring at room temperature for 5 hours. Then, dichloromethane was evaporated under reduced pressure and the obtained residue was column-chromatographed (hexane/ethyl acetate=1/1) to yield the compound 25-1 (400 mg, 82%) as a white solid.

Workup

  1. customto be subjected to the hydrogenation reaction (1 atm)
  2. customAfter the completion of the reaction
  3. filtrationthe resulting mixture was filtered
  4. customevaporated under reduced pressure
  5. customto remove methanol
  6. dissolutionThe obtained residue was dissolved in dichloromethane (3 ml) and to the solution
  7. stirringby stirring at room temperature for 5 hours
  8. customThen, dichloromethane was evaporated under reduced pressure
  9. customthe obtained residue was column-chromatographed (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-31616fb5ae9b449c9390beb0b207c5ce
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

Loading…