Phosphorus pentachloride → 2-[2-(5-Nitro-2-furyl)vinyl]-4-chloroquinazoline

HRID 918240Notes

Reaction equation

HRID 918240 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[N+:7]([C:10]1[O:14][C:13]([CH:15]=[CH:16][C:17]2[NH:26][C:25](=O)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)=[CH:12][CH:11]=1)([O-:9])=[O:8]>P(Cl)(Cl)(Cl)=O>[N+:7]([C:10]1[O:14][C:13]([CH:15]=[CH:16][C:17]2[N:26]=[C:25]([Cl:2])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 1361143292-[2-(5-nitro-2-furyl)vinyl]-4-(3H)quinazolinone

Product 1

HCID 536340792-[2-(5-Nitro-2-furyl)vinyl]-4-chloroquinazolineYield 67%

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 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 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 melting at 252°-4°C with decomposition. The product was recrystallized from toluene (large volumes are required) or was extracted in a Soxhlet extractor with toluene to obtain yellow crystals of 2-[2-(5-nitro-2-furyl)vinyl]-4-chloroquinazoline melting at 264°-5°C with decomposition.

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 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-af20cb1c6b694e3b96d3606b17aa2b9f
Source dataset
uspto-grants-1976_07
Patent number
US03970648

Reaction notes

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