Dimethylformamide → 4-Chloro-6,7-dimethoxyquinazoline

HRID 1767735Notes

Reaction equation

HRID 1767735 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][CH2:19]C1C=CC=CC=1)[N:14]=[CH:13][NH:12][C:11]2=O.S(Cl)([Cl:29])=O>>[Cl:29][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 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

HCID 27693644-Chloro-6,7-dimethoxyquinazolineYield 90%

Procedure

Dimethylformamide (0.2 ml) was added dropwise to a solution of 6-methoxy-7-benzyloxy-3,4-dihydroquinazolin-4-one (5.00 g, 17.9 mmol) in thionyl chloride (100 ml) and the reaction was heated at reflux for 1 hour. The reaction was cooled, excess thionyl chloride was removed in vacuo and the residue was azeotroped with toluene (3×50 ml) to remove the last of the thionyl chloride. The residue was taken up in dichloromethane (550 ml), the solution was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and water (100 ml) and the organic phase was dried over magnesium sulphate. Solvent evaporation in vacuo yielded 4-chloro-6,7-dimethoxyquinazoline (4.80 g, 90% yield) as a pale brown solid:

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction was cooled
  4. customexcess thionyl chloride was removed in vacuo
  5. customthe residue was azeotroped with toluene (3×50 ml)
  6. customto remove the last of the thionyl chloride
  7. washthe solution was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and water (100 ml)
  8. dry with materialthe organic phase was dried over magnesium sulphate
  9. customSolvent evaporation in vacuo

Sources & evidence

ORD record
ord-3936bb76062c4b20afb58ebcd5eca29f
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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