Water → 4-Chloro-6,7-dimethoxyquinazoline

HRID 1893877Notes

Reaction equation

HRID 1893877 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.O.C([O-])([O-])=O.[Na+].[Na+].S(Cl)([Cl:25])=O>CN(C)C=O.ClCCl>[Cl:25][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

7

Reactant 4

HCID 962WaterHCID 10340Sodium Carbonate2×HCID 24386Thionyl ChlorideHCID 1354950166,7-Dimethoxy-3H-quinazolin-4-one

Product 1

HCID 27693644-Chloro-6,7-dimethoxyquinazolineYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A 6,7-dimethoxyquinazolin-4(3H)-one suspension (2a) (0.79 g, 3.83 mmol) in thionyl chloride (7.0 mL) containing 10 drops of N,N-dimethylformarnide (DMF) was agitated and heated under reflux for three hours, until a solution was obtained. The reaction mixture was left cooling at room temperature. The reaction environment was diluted in dichloromethane and water (160 mL) and left in ice bath. The material was treated under agitation with 30 mL of saturated Na2CO3 solution. Na2CO3 was carefully added until pH was adjusted to 7-8 range. Then, the aqueous phase was extracted with CH2Cl2 (2×30 mL), and the organic phase compound was washed with salt solution (2×10 mL), dried over magnesium sulfate, filtered, and the solvent was evaporated in a rotatory evaporator in order to provide 6,7-dimethoxy-4-chloroquinazoline (3a) as a yellow solid (0.68 g, 3.03 mmol, 79%), which was used without purification in the next stage: melting point 185-187° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for three hours, until a solution
  3. customwas obtained
  4. waitThe reaction mixture was left
  5. extractionThen, the aqueous phase was extracted with CH2Cl2 (2×30 mL)
  6. washthe organic phase compound was washed with salt solution (2×10 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated in a rotatory evaporator in order

Sources & evidence

ORD record
ord-e9adbadd2afa4a8fb839562fe02f9884
Source dataset
uspto-grants-2013_08
Patent number
US08513267B2

Reaction notes

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