Formamide → 4-Chloroquinazoline

HRID 487577

Reaktionsgleichung

Reaktionsgleichung von HRID 487577
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][CH:2]=1.C(N)=O.CN(C=NC=[N+](C)C)C.[Cl-].OC1C2C(=CC=CC=2)N=CN=1.P(Cl)(Cl)(Cl)(Cl)[Cl:36]>O1CCOCC1.P(Cl)(Cl)(Cl)=O>[Cl:36][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][N:3]=1

Komponenten

8

Edukt 5

HCID 713FormamideHCID 9210QuinazolineHCID 24819Phosphorus pentachlorideHCID 11008255Gold's ReagentHCID 178517962HCID 178517962, Verbindung

Produkt 1

HCID 788644-Chloroquinazoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24813Phosphorus oxychlorideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Quinazoline starting materials are commercially available or readily prepared using conventional procedures. For example, 4-hydroxy quinazolines can be prepared from commercially available anthranilic acids via condensation with excess formamide at reflux (M. Endicott et al. J. Am. Chem. Soc., 1946, 68, 1299). Alternatively hydroxy quinazolines can be prepared in dioxane at reflux using Gold's reagent (J. Gupton; Correia, K.; Hertel, G. Synthetic Communications, 1984, 14, 1013). Once in hand, the 4-hydroxy quinazoline is chlorinated under standard conditions, using for example phosphorus pentachloride in phosphorus oxychloride, to provide 4-chloroquinazoline starting materials. The 4-hydroxy quinazoline derivatives can advantageously be chlorinated using the chlorinating reagents and procedure disclosed in U.S. Pat. No. 4,230,644.

Aufarbeitung

  1. customreadily prepared
  2. temperatureat reflux (M. Endicott et al. J. Am. Chem. Soc., 1946, 68, 1299)
  3. temperatureat reflux

Quellen und Nachweise

ORD-Eintrag
ord-6a3211e780de4b41a12fb9630be8eae3
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296484

Verknüpfte Notizen

Wird geladen…