Thionyl Chloride → 4-Chloro-6,7-dimethoxyquinazoline

HRID 1357680Notes

Reaction equation

HRID 1357680 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][NH:7][C:6]2=O.S(Cl)([Cl:18])=O>CN(C=O)C>[Cl:18][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1354950166,7-Dimethoxy-3H-quinazolin-4-one

Product 1

HCID 27693644-Chloro-6,7-dimethoxyquinazolineYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 6,7-dimethoxy-3,4-dihydroquinazolin-4-one (2.06 g), thionyl chloride (20 ml) and DMF (1 drop) was stirred and heated to reflux for 2 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution. The organic phase was washed with water, dried over magnesium sulphate, filtered and evaporated to dryness. The residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and ethyl acetate as the eluant to give 4-chloro-6,7-dimethoxyquinazoline (0.6 g, 27%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customThe mixture was evaporated
  4. customthe residue was partitioned between ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified by column chromatography
  10. temperatureusing increasingly polar mixtures of methylene chloride and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-aceac7beb5a7432b8741c493883b9e52
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

Loading…