3,4-Dichloroaniline → HCID 178518005, Verbindung
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]=[C:7]2[OH:13].[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[Cl:22])[NH2:18]>CN1CCCC1=O>[Cl:14][C:15]1[CH:16]=[C:17]([NH:18][C:9]2[N:8]=[C:7]([OH:13])[C:6]3[C:11](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=3)[N:10]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 8-bromo-2-chloroquinazolin-4-ol (0.37 g) and 3,4-dichloroaniline (0.69 g) in 1-methyl-2-pyrrolidinone (8 mL) was heated at 140° C. for 3 h. The mixture was then cooled to room temperature and poured onto ice/water (100 mL). The precipitate which formed was isolated by filtration, washed sequentially with water and diethyl ether, then was dried in vacuo to afford the title compound (0.46 g). 1H NMR (300 MHz, DMSO-d6): δ11.14 (s, 1H), 9.22 (s, 1H), 8.80 (d, J=2.4 Hz, 1H), 8.04 (d, J=7.8 Hz, 1H), 7.99 (d, J=7.8 Hz, 1H), 7.57-7.51 (m, 2H), 7.20-7.18 (m, 1H). HPLC Method B: 9.90 min. MS (APCI+): m/z 386, 388. (APCI−): m/z 384, 386. The starting material 8-Bromo-2-chloroquinazolin-4-ol was prepared as follows: