Toluene → 4-Chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline

HRID 1791594Notes

Reaction equation

HRID 1791594 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[N:9]=[CH:8][NH:7][C:6]2=O.CN(C=O)C.C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+].S(Cl)([Cl:41])=O>>[Cl:41][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

6

Reactant 5

HCID 1140TolueneHCID 6228DimethylformamideHCID 24386Thionyl Chloride2×HCID 516892Sodium BicarbonateHCID 1357631126-Methoxy-7-(3-methylsulphonylpropoxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 218748234-Chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazolineYield 88%

Procedure

6-Methoxy-7-(3-methylsulphonylpropoxy)-3,4-dihydroquinazolin-4-one (3.6 g, 11.5 mmol) was suspended in thionyl chloride (40 ml). DMF (1.8 ml) was added under argon and the mixture was heated at reflux for 1.5 hours. The thionyl chloride was eliminated by several azeotropic distillations using toluene. The solid residue was suspended in ice/water and a saturated solution of sodium hydrogen carbonate was added to adjust the mixture to pH7. The solid was collected by filtration, washed with water and dried in a vacuum dessicator over phosphorus pentoxide to give 4-chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (3.35 g, 88%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. dry with materialdried in a vacuum dessicator over phosphorus pentoxide

Sources & evidence

ORD record
ord-ccd25b557cf14e1f8fe5ba6a11a356ea
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

Loading…