Réaction #804535

Équation de réaction

2-(3,4,5-trimethoxyphenyl)quinazolin-4-ol

dichloromethane

(COCl)2

→

4-chloro-2-(3,4,5-trimethoxyphenyl)quinazoline

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreInto a 1-L 3-necked round-bottom flask, was placed
2. 2
   TempératureThe resulting solution was heated
3. 3
   Températureto reflux for 1 h in an oil bath
4. 4
   AutreThe reaction was then quenched by the addition of 50 mL of sodium bicarbonate (sat.)
5. 5
   ExtractionThe resulting solution was extracted with 2×100 mL of dichloromethane
6. 6
   SéchageThe mixture was dried over anhydrous sodium sulfate
7. 7
   Concentrationconcentrated under vacuum
8. 8
   AutreThis resulted in 10 g (78.7%) of 4-chloro-2-(3,4,5-trimethoxyphenyl)quinazoline as a white solid

Mode opératoire

Into a 1-L 3-necked round-bottom flask, was placed 2-(3,4,5-trimethoxyphenyl)quinazolin-4-ol (12 g, 38.5 mmol, 1.00 equiv), dichloromethane (500 mL) and N,N-dimethylformamide (0.5 mL). This was followed by the addition of (COCl)2 (15 g) dropwise with stirring at 0° C. The resulting solution was heated to reflux for 1 h in an oil bath. The reaction was then quenched by the addition of 50 mL of sodium bicarbonate (sat.). The resulting solution was extracted with 2×100 mL of dichloromethane and the organic layers combined. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate:dichloromethane:petroleum ether (1:1:4). This resulted in 10 g (78.7%) of 4-chloro-2-(3,4,5-trimethoxyphenyl)quinazoline as a white solid. MS (ESI) m/z 332 ([M+H]+).

Source