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

HRID 454059Notes

Reaction equation

HRID 454059 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-b257c3d5c4ad4157b9b9d418ebfc4f79
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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