Reaktion #356935

Reaktionsgleichung

Phosphorous oxychloride

2,6-diphenyl-3H-pyrimidin-4-one

phosphorous pentachloride

→

needles

Ausbeute 65.0%

4-Chloro-2,6-diphenyl-pyrimidine

Ausbeute 65.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 3 hours
2. 2
   SonstigeThe reaction mixture was then quenched
3. 3
   workup.ADDITIONby pouring into ice-water
4. 4
   Extraktionextracted with ethyl acetate (3×150 mL)
5. 5
   WaschenThe combined organic layers were washed with water and brine
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto give a yellow solid
9. 9
   SonstigeThis was recrystallised from hot ethanol

Vorschrift

Phosphorous oxychloride (9.30 mL, 99.8 mmol, 7.5 eq.) was added dropwise to 2,6-diphenyl-3H-pyrimidin-4-one (10) (3.3 g, 13.3 mmol) in a vigorous reaction. To this mixture was added slowly phosphorous pentachloride (2.77 g, 13.3 mmol, 1 eq.) and the reaction mixture was stirred at reflux for 3 hours. The reaction mixture was then quenched by pouring into ice-water, and extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with water and brine, dried (MgSO4) and then concentrated to give a yellow solid. This was recrystallised from hot ethanol to give fine white needles (65%). 1H NMR δ (CDCl3): 8.60-8.18 (m, 5H, Ar), 7.63 (s, 1H, Ar), 7.51-7.57 (m, 5H, Ar).

Quelle