Phosphorus oxychloride → 4-Chloroquinazoline

HRID 2080028Notes

Reaction equation

HRID 2080028 reaction equation
P(Cl)(Cl)(Cl)=O.P(Cl)(Cl)(Cl)(Cl)[Cl:7].O[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1>>[Cl:7][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178517962HCID 178517962, compound

Product 1

HCID 788644-ChloroquinazolineYield 93.3%

Procedure

Phosphorus oxychloride (64 mL, 687 mmol) and phosphorus pentachloride (14.89 g, 71.50 mmol) were added to 4-hydroxyquinazoline (7.94 g, 52.3 mmol), and the solution was stirred for 20 minutes under reflux. The reaction mixture was evaporated in vacuo, and the residue was dissolved in chloroform. The chloroform solution was poured on an ice bath, concentrated aqueous ammonia was added to adjust the pH to 10, then, the solution was partitioned. The aqueous layer was extracted with chloroform, and the combined chloroform layers were washed with water. The organic layer was dried over anhydrous magnesium sulfate, then, evaporated in vacuo, and the title compound (8.03 g,48.8 mmol, 93%) was obtained. This was used in the next reaction without purification.

Workup

  1. temperatureunder reflux
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in chloroform
  4. additionThe chloroform solution was poured on an ice bath
  5. additionconcentrated aqueous ammonia was added
  6. customthe solution was partitioned
  7. extractionThe aqueous layer was extracted with chloroform
  8. washthe combined chloroform layers were washed with water
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-0e26920eeef6497a918a0d069e37b886
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…