Reaktion #743484

Reaktionsgleichung

Vaniline

benzylamine

phenethylisothiocyanate

→

compound 25-1

Ausbeute 82.0%

1-benzyl-1-(4-hydroxy-3-methoxybenzyl)-3-phenethylthiourea

Ausbeute 82.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto be subjected to the hydrogenation reaction (1 atm)
2. 2
   SonstigeAfter the completion of the reaction
3. 3
   Filtrationthe resulting mixture was filtered
4. 4
   Sonstigeevaporated under reduced pressure
5. 5
   Sonstigeto remove methanol
6. 6
   workup.DISSOLUTIONThe obtained residue was dissolved in dichloromethane (3 ml) and to the solution
7. 7
   workup.STIRRINGby stirring at room temperature for 5 hours
8. 8
   SonstigeThen, dichloromethane was evaporated under reduced pressure
9. 9
   Sonstigethe obtained residue was column-chromatographed (hexane/ethyl acetate=1/1)

Vorschrift

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.

Quelle