反応 #721859

反応方程式

hexane

7-acetoxy-6-methoxy-3,4-dihydroquinazolin-4-one

thionyl chloride

5-Benzyloxy-2-fluoro-4-methylaniline

→

7-acetoxy-4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline

収率 43.0%

溶媒

isopropanol

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 2 hours
3. 3
   その他The excess thionyl chloride was removed by evaporation
4. 4
   その他the residue azeotroped with toluene
5. 5
   その他The residue was partitioned between methylene chloride and saturated aqueous sodium hydrogen carbonate solution
6. 6
   その他The organic phase was separated
7. 7
   乾燥dried (MgSO4)
8. 8
   その他the solvent removed by evaporation
9. 9
   温度the mixture heated
10. 10
    温度at reflux for 2 hours
11. 11
    温度to cool
12. 12
    ろ過the precipitated product collected by filtration

実験手順

A mixture of 7-acetoxy-6-methoxy-3,4-dihydroquinazolin-4-one (1.69 g, 7.2 mmol), thionyl chloride (50 ml) and DMF (3 drops) was heated at reflux for 2 hours. The excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The residue was partitioned between methylene chloride and saturated aqueous sodium hydrogen carbonate solution. The organic phase was separated, dried (MgSO4) and the solvent removed by evaporation. 5-Benzyloxy-2-fluoro-4-methylaniline (1.8 g, 7.8 mmol) in isopropanol (50 ml) was added to the residue and the mixture heated at reflux for 2 hours. The mixture was allowed to cool, hexane added and the precipitated product collected by filtration to give 7-acetoxy-4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline (1.34 g, 43%).

出典