Thionyl Chloride → 4-Chloro-6-fluoroquinazoline

HRID 618674Notes

Reaction equation

HRID 618674 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=O.S(Cl)([Cl:15])=O>CN(C=O)C>[Cl:15][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1354805206-fluoroquinazolin-4-ol

Product 1

HCID 130594574-Chloro-6-fluoroquinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

6-Fluoro-3,4-dihydroquinazolin-4-one (1.0 g) was suspended in a mixture of thionyl chloride (10 ml) and DMF (1to 2 drops). The mixture was heated to reflux for 2 to 3 hours and allowed to cool. Solvent was removed by evaporation and the residue was dried under vacuum to give 4-chloro-6-fluoroquinazoline which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 to 3 hours
  3. temperatureto cool
  4. customSolvent was removed by evaporation
  5. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-6a31bf73d00446fb920cb7bc90b87c83
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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