Formamide → 4-Chloroquinazoline

HRID 35834

Reaction equation

HRID 35834 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 788644-Chloroquinazoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-f16f3c2a2f8d4f759a391b79a9ed7598
Source dataset
uspto-grants-1995_05
Patent number
US05411963

Linked notes

Loading…