Phosphorus pentachloride → 4-Chloroquinazoline

HRID 1751874Notes

Reaction equation

HRID 1751874 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[NH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:13]>P(Cl)(Cl)(Cl)=O>[Cl:13][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

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 1354087534(1H)-Quinazolinone

Product 1

HCID 788644-Chloroquinazoline

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

4-Quinazolone (5 g, 34.2 mmol), phosphorus pentachloride (10.26 g, 47.9 mmol) and phosphorus oxychloride (40 ml) were refluxed for two hours at 115-118 C. The phosphorus oxychloride was removed in vacuo and the residue was extracted in ether. The entire mixture was then poured into a vessel containing crushed ice and again extracted with ether. The ether layer was then washed with sodium bicarbonate and dried. The ether was then removed under reduced pressure and the crude material was recrystallized from hexanes to afford the product.

Workup

  1. customThe phosphorus oxychloride was removed in vacuo
  2. extractionthe residue was extracted in ether
  3. additionThe entire mixture was then poured into a vessel
  4. additioncontaining
  5. customcrushed ice
  6. extractionagain extracted with ether
  7. washThe ether layer was then washed with sodium bicarbonate
  8. customdried
  9. customThe ether was then removed under reduced pressure
  10. customthe crude material was recrystallized from hexanes
  11. customto afford the product

Sources & evidence

ORD record
ord-316c34f86dc14c91bcea3695ef652541
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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