Reaktion #1838110

Reaktionsgleichung

N-(2-chloroethyl)benzamide

Phosphorus pentachloride

2,4-diisopropyldibenzo[b,d]thiophen-3-amine

→

title product

Ausbeute 50.0%

1-(2,4-diisopropyldibenzo[b,d]thiophen-3-yl)-2-phenyl-4,5-dihydro-1H-imidazole

Ausbeute 50.0%

Lösungsmittel

m-xylene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturto reflux under nitrogen for 2 h
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturto reflux for 20 h
5. 5
   TemperaturAfter cooling
6. 6
   Filtrationthe precipitate was filtered
7. 7
   Sonstigethe solid imidazoline product was collected
8. 8
   Waschenwashed with toluene
9. 9
   workup.DISSOLUTIONThe resultant crude product was dissolved in methylene chloride
10. 10
    Waschenwashed twice with 50% NaOH
11. 11
    TrocknenThe organic layer was dried over MgSO4
12. 12
    Filtrationfiltered
13. 13
    Einengenconcentrated under reduced pressure

Vorschrift

N-(2-chloroethyl)benzamide (4.3 g, 23.42 mmol), was dissolved in 50 mL anhydrous m-xylene under nitrogen. Phosphorus pentachloride (7.31 g, 35.1 mmol) was then carefully added and the mixture heated to reflux under nitrogen for 2 h. The solution was allowed to cooled to room temperature and 2,4-diisopropyldibenzo[b,d]thiophen-3-amine (7.30 g, 25.8 mmol) was added. The reaction mixture was heated to reflux for 20 h. After cooling, the precipitate was filtered and the solid imidazoline product was collected and washed with toluene followed by hexanes. The resultant crude product was dissolved in methylene chloride and washed twice with 50% NaOH. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to afford title product (4.8 g, 50%).

Quelle