Sodium Thiosulfate → 2-(4-Chloro-2-ethylsulfonylphenyl)-4-ethylamino-7-trifluoromethylquinazoline
Reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)[CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:28]=[C:27]([NH:29][CH2:30][CH3:31])[C:26]3[C:21](=[CH:22][C:23]([C:32]([F:35])([F:34])[F:33])=[CH:24][CH:25]=3)[N:20]=2)=[C:15](SCC)[CH:14]=1.[S:39]([O-:43])([O-])(=[O:41])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:28]=[C:27]([NH:29][CH2:30][CH3:31])[C:26]3[C:21](=[CH:22][C:23]([C:32]([F:34])([F:33])[F:35])=[CH:24][CH:25]=3)[N:20]=2)=[C:15]([S:39]([CH2:2][CH3:3])(=[O:43])=[O:41])[CH:14]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
375 mg of 3-chloroperbenzoic acid (purity of 65% or more) was added to a mixture of 306 mg of 2-(4-chloro-2-ethylsulfanylphenyl)-4-ethylamino-7-trifluoromethylquinazoline and 5 ml of chloroform, under ice cooling, and the mixture was stirred at room temperature for 4 hours. A 10% aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 270 mg of 2-(4-chloro-2-ethylsulfonylphenyl)-4-ethylamino-7-trifluoromethylquinazoline (Compound of Present Invention 16).
Workup
- extractionthe mixture was extracted with chloroform
- washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-21e281cad50a41b299b852b691175d44
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328121B1
Reaction notes
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