1,2-Dichloroethane → 2,6-Dichloroquinazoline

反応式

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](N)[N:6]=[CH:5]2.C(O[N+]([O-])=O)(C)(C)C.C([O-])(O)=O.[Na+].[Cl:26]CCCl>>[Cl:26][C:7]1[N:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

参加物

反応物 4

HCID 111,2-Dichloroethane

HCID 164756Nitric acid, 1,1-dimethylethyl ester

HCID 516892Sodium Bicarbonate

HCID 211839426-Chloroquinazolin-2-amine

生成物 1

HCID 124139282,6-Dichloroquinazoline収率 20%

反応条件

温度: 60 °C

実験手順

To a suspension of 6-chloro-quinazolin-2-ylamine (110) (2.8 g, 15.8 mmol) and SbCl3 (7.2 g, 32 mmol) in 1,2-dichloroethane (100 mL) was added tert-butylnitrate (6.2 ml, 52 mmol) and heated at 60° C. for 3 h under nitrogen atmosphere. To the mixture was added aqueous saturated NaHCO3 and the mixture was filtered off and filtrate was extracted with CHCl3. The organic layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by silica gel column chromatography, using CHCl3/EtOAc (9:1, v/v) as eluent to give 2,6-dichloro-quinazoline (111) (0.65 g, 3.12 mmol, 20% yield).