Sodium Thiosulfate → 2-(2-Ethylsulfinylphenyl)-4-propylamino-7-trifluoromethylquinazoline

HRID 1775261Notes

Reaction equation

HRID 1775261 reaction equation
Cl[C:2]1C=CC=C(C(OO)=[O:9])[CH:3]=1.[CH2:12]([S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:30]=[C:29]([NH:31][CH2:32][CH2:33][CH3:34])[C:28]2[C:23](=[CH:24][C:25]([C:35]([F:38])([F:37])[F:36])=[CH:26][CH:27]=2)[N:22]=1)[CH3:13].[S:39]([O-:43])([O-])(=[O:41])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:12]([S:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:30]=[C:29]([NH:31][CH2:32][CH2:33][CH3:34])[C:28]2[C:23](=[CH:24][C:25]([C:35]([F:38])([F:37])[F:36])=[CH:26][CH:27]=2)[N:22]=1)=[O:9])[CH3:13].[CH2:2]([S:39]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:30]=[C:29]([NH:31][CH2:32][CH2:33][CH3:34])[C:28]2[C:23](=[CH:24][C:25]([C:35]([F:38])([F:37])[F:36])=[CH:26][CH:27]=2)[N:22]=1)(=[O:43])=[O:41])[CH3:3]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 1182058272-(2-Ethylsulfanylphenyl)-4-propylamino-7-trifluoromethylquinazoline

Product 2

HCID 1182058252-(2-Ethylsulfinylphenyl)-4-propylamino-7-trifluoromethylquinazolineHCID 1182058362-(2-Ethylsulfonylphenyl)-4-propylamino-7-trifluoromethylquinazoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

281 mg of 3-chloroperbenzoic acid (purity of 65% or more) was added to a mixture of 305 mg of 2-(2-ethylsulfanylphenyl)-4-propylamino-7-trifluoromethylquinazoline and 4 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 174 mg of 2-(2-ethylsulfinylphenyl)-4-propylamino-7-trifluoromethylquinazoline (Compound of Present Invention 9) and 100 mg of 2-(2-ethylsulfonylphenyl)-4-propylamino-7-trifluoromethylquinazoline (Compound of Present Invention 10).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc1f60a94aa44345a78b32c1736676e5
Source dataset
uspto-grants-2016_02
Patent number
US09260436B2

Reaction notes

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