Phosphorus pentachloride → 8-Chloro-2H-[1,3]dioxolo[4,5-g]quinazoline

HRID 1249744Notes

Reaction equation

HRID 1249744 reaction equation
[O:1]1[C:5]2=[CH:6][C:7]3[C:8](=O)[NH:9][CH:10]=[N:11][C:12]=3[CH:13]=[C:4]2[O:3][CH2:2]1.P(Cl)(Cl)(Cl)(Cl)[Cl:16]>P(Cl)(Cl)(Cl)=O>[Cl:16][C:8]1[C:7]2[CH:6]=[C:5]3[O:1][CH2:2][O:3][C:4]3=[CH:13][C:12]=2[N:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 135679869HCID 135679869, compound

Product 1

HCID 149353678-Chloro-2H-[1,3]dioxolo[4,5-g]quinazolineYield 74%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 7H-[1,3]dioxolo[4,5-g]quinazolin-8-one (0.550 g, 2.78 mmol) and phosphorus pentachloride (0.800 g, 3.84 mmol) in 3 mL phosphorus oxychloride was heated to a gentle reflux for 2.5 hours. Solvent was removed in vacuo, and azeotroped with toluene. Residue was dissolved in ethyl acetate and washed with 5% sodium bicarbonate solution and then filtered, and then solvent was removed in vacuo to give 8-chloro-[1,3]dioxolo[4,5-g]quinazoline (0.400 g, 74%).

Workup

  1. temperaturewas heated to
  2. temperaturea gentle reflux for 2.5 hours
  3. customSolvent was removed in vacuo
  4. customazeotroped with toluene
  5. dissolutionResidue was dissolved in ethyl acetate
  6. washwashed with 5% sodium bicarbonate solution
  7. filtrationfiltered
  8. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-ef359185d5604517834247d5b7313891
Source dataset
uspto-grants-2002_01
Patent number
US06335344B1

Reaction notes

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