Sodium Thiosulfate → 5-((Trifluoromethyl)sulfinyl)benzo[d]oxazole

HRID 1750063Notes

Reaction equation

HRID 1750063 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]([S:16][C:17]1[CH:18]=[CH:19][C:20]2[O:24][CH:23]=[N:22][C:21]=2[CH:25]=1)([F:15])[F:14].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:15][C:13]([F:12])([F:14])[S:16]([C:17]1[CH:18]=[CH:19][C:20]2[O:24][CH:23]=[N:22][C:21]=2[CH:25]=1)=[O:6]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 118035693HCID 118035693, compound

Product 1

HCID 1180354975-((Trifluoromethyl)sulfinyl)benzo[d]oxazoleYield 37.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.71 g of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 0.50 g of 5-trifluoromethylsulfanylbenzoxazole and 3 ml of chloroform under ice cooling, and then the mixture was stirred at room temperature for 1 day. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.20 g of 5-trifluoromethylsulfinylbenzoxazole.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5225cd764aed4c14b0fbc7a37179eacb
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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