Thionyl Chloride → 4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline
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][N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])[N:9]=[CH:8][NH:7][C:6]2=O.S(Cl)([Cl:26])=O>CN(C=O)C>[Cl:26][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1Participants
4
Procedure
6-Methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazolin-4-one (2.24 g, 6.6 mmol) was taken up in thionyl chloride (25 ml) and treated with DMF (5 drops). The resulting solution was then heated at reflux for 1 hour followed by cooling to ambient temperature. The excess thionyl chloride was removed by evaporation followed by azeotroping with toluene (3×). The residue was basified with saturated aqueous sodium hydrogen carbonate solution (to pH8) and extracted twice with ethyl acetate. The organic solution was washed with water, brine, dried (MgSO4) and evaporated to dryness to give 4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline (1.90 g, 80%).
Workup
- temperatureThe resulting solution was then heated
- temperatureat reflux for 1 hour
- customThe excess thionyl chloride was removed by evaporation
- customby azeotroping with toluene (3×)
- extractionextracted twice with ethyl acetate
- washThe organic solution was washed with water, brine
- dry with materialdried (MgSO4)
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-3d7a6b98163b4950bbc754421806b1c0
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074800B1
Reaction notes
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