Reacción #2487447

Ecuación de reacción

2-(4-chlorophenyl)-7-trifluoromethyl-3H-quinazolin-4-one

phosphorus oxychloride

→

4-Chloro-2-(4-chloro-phenyl)-7-trifluoromethylquinazoline

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe suspension was then heated
2. 2
   Temperaturaat reflux for 2 h
3. 3
   Otroevaporated under reduced pressure
4. 4
   workup.DISSOLUTIONThe remaining solid was dissolved in dioxane (1 L)
5. 5
   workup.ADDITIONan aqueous solution of sodium hydroxide (50 mL, 10% weight/weight (w/w)) was added dropwise
6. 6
   Temperaturamaintaining the internal temperature≦10° C.)
7. 7
   workup.ADDITIONWater (1 L) was then added to the resultant suspension
8. 8
   workup.ADDITIONfollowed by the dropwise addition of a further quantity of aqueous sodium hydroxide (90 mL, 10% w/w)
9. 9
   OtroThe precipitate was isolated by vacuum filtration
10. 10
    Lavadowashing with water (3×500 mL)
11. 11
    Otrodried under vacuum (10 mbar, 50° C.)
12. 12
    Otro4.7 min, 343 (M+)

Procedimiento

To a stirred suspension of 2-(4-chlorophenyl)-7-trifluoromethyl-3H-quinazolin-4-one (50 g, 0.15 mol) in dioxane (400 mL) was added dropwise phosphorus oxychloride (43 mL, 0.46 mol). The suspension was then heated at reflux for 2 h then allowed to cool to room temperature and evaporated under reduced pressure. The remaining solid was dissolved in dioxane (1 L) and an aqueous solution of sodium hydroxide (50 mL, 10% weight/weight (w/w)) was added dropwise maintaining the internal temperature≦10° C.). Water (1 L) was then added to the resultant suspension followed by the dropwise addition of a further quantity of aqueous sodium hydroxide (90 mL, 10% w/w). The precipitate was isolated by vacuum filtration washing with water (3×500 mL) and dried under vacuum (10 mbar, 50° C.). Yield=49 g, 93%; LC-MS: 4.7 min, 343 (M+); 1H NMR (dimethylsulfoxide (DMSO)-d6) δ 7.68 (d, 2 H, J=8.9 Hz), 8.12 (dd, 1 H, J=8.9, 1.8 Hz), 8.48-8.54 (m, 4 H).

Fuente