Reaktion #6038

Reaktionsgleichung

potassium tert-butoxide

tetrahydrofuran

methyl isothiocyanate

tetrahydrofuran

2-[4-(1-imidazolyl)-phenyl]propionitrile

tetrahydrofuran

→

N-methyl-2-[4-(1-imidazolyl)-phenyl]-2cyanothiopropionamide

Ausbeute 54.4%

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the mixture
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hours
3. 3
   Extraktionthe mixture was extracted with 20 ml of ethyl acetate
4. 4
   Sonstigedried
5. 5
   Sonstigecondensed under reduced pressure
6. 6
   Sonstigepurified by silica gel chromatography and condensed
7. 7
   Temperaturthe suspension was refluxed
8. 8
   Temperaturunder heating for 0.5 hour
9. 9
   Filtrationa solid was collected by filtration

Vorschrift

To a 10 ml tetrahydrofuran solution containing 1.00 g (5.1 mmole) of 2-[4-(1-imidazolyl)-phenyl]propionitrile was added a 10 ml tetrahydrofuran solution containing 0.69 g (6.2 mmole) of potassium tert-butoxide at 0 C. After stirring for 0.5 hour, a 5 ml tetrahydrofuran solution containing 0.45 g (6.2 mmole) of methyl isothiocyanate was added to the mixture and the mixture was stirred at room temperature for 2 hours. Water was added to the mixture and the mixture was extracted with 20 ml of ethyl acetate, dried and condensed under reduced pressure, and then purified by silica gel chromatography and condensed. The resulting condensate was suspended in 30 ml of toluene and the suspension was refluxed under heating for 0.5 hour and a solid was collected by filtration to obtain 0.75 g (yield: 54 %) of N-methyl-2-[4-(1-imidazolyl)-phenyl]-2cyanothiopropionamide as a crystalline solid.

Quelle