Phosphorus pentachloride → HCID 72829569, compound

HRID 2217994Notes

Reaction equation

HRID 2217994 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH:18]=[CH:19][C:20]1[O:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)[NH:12][C:11]2=O>P(Cl)(Cl)(Cl)=O>[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH:18]=[CH:19][C:20]1[O:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)[N:12]=[C:11]2[Cl:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 136335823HCID 136335823, compound

Product 1

HCID 72829569HCID 72829569, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A 500 ml 3 necked flask fitted with a stirrer, reflux condenser and protected by a calcium chloride trap was charged with 9.0 g of phosphorus pentachloride (0.043 mole) and 70 ml of phosphorus oxychloride and the mixture stirred. To this 11.3 g (0.04 mole) of 6-fluoro-2-[2-(5-nitro-2-furyl)vinyl]-4-(3H)quinazolinone was added and rinsed into the flask with 15 ml of phosphorus oxychloride. The mixture was heated under reflux for 4 hours, cooled in an ice bath and diluted with 150 ml of diethyl ether. The 6-fluoro-2-[2-(5-nitro-2-furyl)vinyl]-4-chloroquinazoline which precipitated was collected by filtration, washed with 100-150 ml of diethyl ether, slurried in 100 ml of diethyl ether and then refiltered to obtain 8.09 g of the desired product.

Workup

  1. temperaturereflux condenser
  2. customprotected by a calcium chloride trap
  3. washrinsed into the flask with 15 ml of phosphorus oxychloride
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 4 hours
  6. temperaturecooled in an ice bath
  7. additiondiluted with 150 ml of diethyl ether
  8. customThe 6-fluoro-2-[2-(5-nitro-2-furyl)vinyl]-4-chloroquinazoline which precipitated
  9. filtrationwas collected by filtration
  10. washwashed with 100-150 ml of diethyl ether

Sources & evidence

ORD record
ord-8aef23125b2e4057af24241d8051657b
Source dataset
uspto-grants-2008_08
Patent number
US07410974B2

Reaction notes

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