Dimethylformamide → 4-Chloro-2-(3-nitrophenyl)quinazoline

Reaktionsgleichung

[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[NH:19][C:18](=O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CN(C=O)C.S(Cl)([Cl:28])=O>>[Cl:28][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:19]=1

Komponenten

Edukt 3

HCID 6228Dimethylformamide

HCID 24386Thionyl Chloride

HCID 1355026292-(3-nitrophenyl)quinazolin-4(3H)-one

Produkt 1

HCID 593619944-Chloro-2-(3-nitrophenyl)quinazoline

Versuchsvorschrift

To a suspension of 2-(3-nitrophenyl)quinazolin-4(3H)-one (5.7 g, 21.32 mmole) in thionyl chloride (70 mL) was added of DMF (2 mL). The reaction mixture was refluxed for 4.5 h. The reaction was then concentrated in vacuo and residue suspended in a mixture of CH2Cl2 (400 mL) and CHCl3 (500 mL). The organic layer was washed with water, saturated NaHCO3, water, brine, dried with Na2SO4 and concentrated in vacuo. The residue was dried under high vacuum to afford 4-chloro-2-(3-nitrophenyl)quinazoline as an off-white solid. (6.0 g, mmol, 97%).