Dimethylformamide → 4-Chloro-6,7-dimethoxyquinazoline

HRID 2213852Notes

Reaction equation

HRID 2213852 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]=[CH:13][NH:12][C:11]2=O.S(Cl)([Cl:23])=O>>[Cl:23][C:11]1[C:10]2[C:15](=[CH:16][C:17]([O:18][CH3:19])=[C:8]([O:7][CH3:6])[CH:9]=2)[N:14]=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1354950166,7-Dimethoxy-3H-quinazolin-4-one

Product 1

HCID 27693644-Chloro-6,7-dimethoxyquinazolineYield 98%

Procedure

Dimethylformamide (0.2 ml) was added dropwise to a solution of 6,7-dimethoxy-3,4-dihydro-quinazolin-4-one (10.0 g, 48.5 mmol) in thionyl chloride (200 ml) and the reaction was heated at reflux for 6 hours. The reaction was cooled, excess thionyl chloride was removed in vacuo and the residue was azeotroped with toluene (2×50 ml) to remove the last of the thionyl chloride. The residue was taken up in dichloromethane (550 ml), the solution was washed with i) saturated aqueous sodium hydrogen carbonate solution (2×250 ml) and ii) brine, and the organic phase was dried over magnesium sulphate. Solvent evaporation in vacuo yielded 4-chloro-6,7-dimethoxyquinazoline (10.7 g, 98% yield) as a white solid:

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 6 hours
  3. temperatureThe reaction was cooled
  4. customexcess thionyl chloride was removed in vacuo
  5. customthe residue was azeotroped with toluene (2×50 ml)
  6. customto remove the last of the thionyl chloride
  7. washthe solution was washed with i) saturated aqueous sodium hydrogen carbonate solution (2×250 ml) and ii) brine
  8. dry with materialthe organic phase was dried over magnesium sulphate
  9. customSolvent evaporation in vacuo

Sources & evidence

ORD record
ord-2ee52c71cecb4c63aa844c78a280fde2
Source dataset
uspto-grants-2006_09
Patent number
US07105669B1

Reaction notes

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