Formamide → 4-Chloroquinazoline

HRID 35834

Reaktionsgleichung

Reaktionsgleichung von HRID 35834
[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-:23].OC1C2C(=CC=CC=2)N=CN=1>O1CCOCC1>[Cl:23][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

6

Edukt 4

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

Produkt 1

HCID 788644-Chloroquinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 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. Gipton; Correia, K.; Hertel, G. Synthetic Communications, 1984, 14, 1013). Once in hand, the 4-hydroxy quinazoline is chlorinated under standard conditions to provide 4-chloroquinazoline starting materials.

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-f16f3c2a2f8d4f759a391b79a9ed7598
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411963

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