1,2-Dichloroethane → 2,6-Dichloroquinazoline

반응식

[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

참가 물질

반응물 4

HCID 111,2-Dichloroethane

HCID 164756Nitric acid, 1,1-dimethylethyl ester

HCID 516892Sodium Bicarbonate

HCID 211839426-Chloroquinazolin-2-amine

생성물 1

HCID 124139282,6-Dichloroquinazoline수율 20%

반응 조건

온도: 60 °C

실험 절차

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).