Thionyl Chloride → 4-chloroquinazoline-6-carbonitrile

HRID 1900644Notes

Reaction equation

HRID 1900644 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-carbonitrile

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-6579ea8e0c0340f78ed6d1c313bc3504
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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