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

HRID 659038Notes

Reaction equation

HRID 659038 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[N:13]=[CH:12][NH:11][C:10]2=O>CN(C)C=O>[Cl:3][C:10]1[C:9]2[C:14](=[CH:15][C:16]([O:17][CH3:18])=[C:7]([O:6][CH3:5])[CH:8]=2)[N:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

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

Product 1

HCID 27693644-Chloro-6,7-dimethoxyquinazolineYield 96.33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
79 °C

Procedure

720.0 g (6.05 mol) of thionyl chloride and 50.0 g (0.243 mol) of 6,7-dimethoxy-3H-quinazoline-4-one were charged into a 2.0 L 4 necked round bottom flask connected to a mechanical stirrer, thermometer socket and double surface reflux condenser. Reaction mass temperature was raised to reflux temperature (78-80° C.). 20.0 ml of dimethyl formamide was added slowly at reflux temperature. Maintained the mass temperature at reflux for 7-8 hours under stirring. Distilled off thionyl chloride completely under vacuum at below 70° C. Cooled the mass temperature to 40° C. to 45° C. under nitrogen atmosphere 1000.0 ml of hexane was charged under stirring. Maintained the mass temperature at 40° C. to 45° C. for 30-45 min. Cooled the mass temperature 25-30° C. Maintained the mass temperature at 25-30° C. for 45-60 min under nitrogen atmosphere. Filtered the solid under nitrogen atmosphere. Solid was washed with 250.0 ml of hexane. Compound was dried in vacuum tray drier containing phosphorus pentoxide at 30-35° C. till the loss on drying is not more than 0.50% w/w. Obtained 52.50 g (yield is 96.33% by theory) of yellow coloured product.

Workup

  1. customconnected to a mechanical stirrer
  2. temperaturethermometer socket and double surface reflux condenser
  3. customReaction mass temperature
  4. temperaturewas raised
  5. temperatureat reflux temperature
  6. temperatureMaintained the mass temperature
  7. temperatureat reflux for 7-8 hours
  8. distillationDistilled off thionyl chloride completely under vacuum at below 70° C
  9. temperatureCooled the mass temperature to 40° C. to 45° C. under nitrogen atmosphere 1000.0 ml of hexane
  10. additionwas charged
  11. stirringunder stirring
  12. temperatureMaintained the mass temperature at 40° C. to 45° C. for 30-45 min
  13. temperatureCooled the mass temperature 25-30° C
  14. temperatureMaintained the mass temperature at 25-30° C. for 45-60 min under nitrogen atmosphere
  15. filtrationFiltered the solid under nitrogen atmosphere
  16. washSolid was washed with 250.0 ml of hexane
  17. customCompound was dried in vacuum tray
  18. additiondrier containing phosphorus pentoxide at 30-35° C. till the loss
  19. customon drying
  20. customObtained 52.50 g (yield is 96.33% by theory) of yellow coloured product

Sources & evidence

ORD record
ord-ad12a0b63e4b41cd8c7cf783478757ae
Source dataset
uspto-grants-2011_12
Patent number
US08080558B2

Reaction notes

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