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

HRID 2084002Notes

Reaction equation

HRID 2084002 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-bce5b803c05942cb99bee95759a7d042
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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