Dimethylformamide → HCID 21936033, Verbindung

Reaktionsgleichung

[C:1]([O:4][CH:5]([CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=O)[NH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:19][CH3:20])(=[O:3])[CH3:2].CN(C=O)C.S(Cl)([Cl:34])=O>>[Cl:34][C:12]1[C:11]2[C:16](=[CH:17][C:8]([O:7][CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[C:9]([O:19][CH3:20])[CH:10]=2)[N:15]=[CH:14][N:13]=1

Komponenten

Edukt 3

HCID 6228Dimethylformamide

HCID 24386Thionyl Chloride

HCID 135763125HCID 135763125, Verbindung

Produkt 1

HCID 21936033HCID 21936033, Verbindung

Versuchsvorschrift

7-(2-Acetoxy-3-(pyrrolidin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (4.7 g) was suspended in thionyl chloride (55 ml), DMF (0.5 ml) was added and the mixture heated at reflex for 1 hour. The thionyl chloride was evaporated under vacuum, toluene was added and the solvent was evaporated. This process was repeated twice. The residue was taken up in ice/water, the pH adjusted to 7.5 with a saturated solution of sodium bicarbonate followed by sodium hydroxide 2N until pH 9 and the aqueous solution extracted twice with dichloromethane. The combined extracts were washed with water and brine, dried over magnesium sulphate and filtered. The filtrate was evaporated under vacuum and the residue triturated with ether to give 4-chloro-7-[2-acetoxy-3-(pyrrolidin-1-yl)propoxy]-6-methoxyquinazoline (4.1 g) as a white foam.