Thionyl Chloride → 4-chloroquinazoline-6-carbonitrile

HRID 1003501Notes

Reaction equation

HRID 1003501 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](=O)[NH2:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.S(Cl)([Cl:17])=O>P(Cl)(Cl)(Cl)=O>[Cl:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178513571HCID 178513571, compound

Product 1

HCID 100127274-chloroquinazoline-6-carbonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture comprising 2 g of 4-hydroxy-6-carbamoylquinazoline, 30 ml of thionyl chloride and 60 ml of phosphorus oxychloride was heated under reflux for 20 hours. The reaction mixture was concentrated under a reduced pressure and the obtained residue was dissolved in 100 ml of ethyl acetate. The obtained solution was washed with water (150 ml), dried over magnesium sulfate and concentrated under a reduced pressure. The obtained residue was introduced into a silica gel column, followed by eluting with ethyl acetate and acetone to give 800 mg of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. concentrationThe reaction mixture was concentrated under a reduced pressure
  4. dissolutionthe obtained residue was dissolved in 100 ml of ethyl acetate
  5. washThe obtained solution was washed with water (150 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. additionThe obtained residue was introduced into a silica gel column
  9. washby eluting with ethyl acetate and acetone

Sources & evidence

ORD record
ord-5bfcc9a67a4148558e1899ffbb600fc4
Source dataset
uspto-grants-2000_04
Patent number
US06046206

Reaction notes

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