Dimethylformamide → 4-Chloro-7-methoxyquinazolin-6-yl acetate--hydrogen chloride (1/1)

HRID 1793432Notes

Reaction equation

HRID 1793432 reaction equation
CN(C)C=O.[C:6]([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]=[CH:15][NH:14][C:13]2=O)(=[O:8])[CH3:7].S(Cl)([Cl:25])=O>>[ClH:25].[Cl:25][C:13]1[C:12]2[C:17](=[CH:18][C:19]([O:20][CH3:21])=[C:10]([O:9][C:6](=[O:8])[CH3:7])[CH:11]=2)[N:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1356819606-Acetoxy-7-methoxy-3H-quinazolin-4-one

Product 1

HCID 220221594-Chloro-7-methoxyquinazolin-6-yl acetate--hydrogen chloride (1/1)Yield 87%

Procedure

Dimethylformamide (0.25 ml) was added dropwise to a solution of 6-acetoxy-7-methoxy-3,4-dihydro-quinazolin-4-one (13.8 g, 59.0 mmol) in thionyl chloride (150 ml) and the reaction was heated at reflux for 1.5 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. Drying in vacuo yielded 4-chloro-6-acetoxy-7-methoxyquinazoline hydrochloride (14.7 g, 87% yield) as a beige solid, which was used without further purification:

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 1.5 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. customDrying in vacuo

Sources & evidence

ORD record
ord-1471d90fa01040128232ed4bb91f676d
Source dataset
uspto-grants-2006_07
Patent number
US07081461B1

Reaction notes

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