4,5-Dichloro-2-fluoroaniline → 4-[(3,4-Dichloro-6-fluorophenyl)amino]-6-nitroquinazoline

HRID 346413

Reaktionsgleichung

Reaktionsgleichung von HRID 346413
[Cl:1][C:2]1[CH:3]=[C:4]([C:6]([F:10])=[CH:7][C:8]=1[Cl:9])[NH2:5].Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)[C:6]([F:10])=[CH:7][C:8]=1[Cl:9]

Komponenten

4

Edukt 2

HCID 2230914,5-Dichloro-2-fluoroanilineHCID 113562574-Chloro-6-nitroquinazoline

Produkt 1

HCID 154809984-[(3,4-Dichloro-6-fluorophenyl)amino]-6-nitroquinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

3,4-Dichloro-6-fluoroaniline (1 equivalent, prepared as described in U.S. Pat. No. 6,126,917) was reacted with 4-chloro-6-nitroquinazoline (3.5 equivalents, prepared by reacting 6-nitroquinazoline with thionyl chloride, according to known procedures), in iso-propylalcohol. After filtration, 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-nitroquinazoline (compound 1) was obtained in 60% yield. m.p.=270–271° C.; MS (m/z): 353.2, 355.2 (M+); 1H-NMR: δ=6.97 (d, 1H), 7.345 (d, 1H), 7.885 (d, 1H), 8.405 (d, 1H), 8.554 (dd, 1H), 8.8 (d, 1H) ppm. HPLC conditions: C-18 column, 55% acetate buffer, PH=3.8/45% acetonitrile, flow=1 ml/min; r.t.=7.15 minutes.

Aufarbeitung

  1. filtrationAfter filtration

Quellen und Nachweise

ORD-Eintrag
ord-83e5d3a1fcd541d29990cc006885a035
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07172749B2

Verknüpfte Notizen

Wird geladen…