Sodium Thiosulfate → HCID 86655224, compound

HRID 1256157Notes

Reaction equation

HRID 1256157 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13]SC)[CH:7]=1)=[O:4].[CH:18]1C=C(Cl)C=C(C(OO)=O)C=1.[S:29]([O-:33])([O-])(=[O:31])=S.[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]([F:16])([F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][S:29]([CH3:18])(=[O:33])=[O:31])[CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86655225HCID 86655225, compound

Product 1

HCID 86655224HCID 86655224, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2,2-trifluoro-N-(3-(2-(methylthio)ethyl)phenyl)acetamide (4 g, 15 mmol) and m-CPBA (7.9 g, 45 mmol) in DCM (30 mL) was heated to reflux overnight. Aqueous solution of sodium thiosulfate (10 mL) was added. The solid was filtered from the mixture solution. The aqueous layer was extracted by ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 2,2,2-trifluoro-N-(3-(2-(methylsulfonyl)ethyl)phenyl)acetamide (4 g, yield 89%). 1H NMR: 400 MHz CDCl3 δ 7.85 (s, 1H), 7.50-7.49 (m, 1H), 7.36-7.28 (m, 2H), 7.07-7.05 (m, 1H), 3.26-3.22 (m, 2H), 3.14-3.10 (m, 2H), 2.79 (s, 3H).

Workup

  1. temperatureto reflux overnight
  2. filtrationThe solid was filtered from the mixture solution
  3. extractionThe aqueous layer was extracted by ethyl acetate 3 times
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0781e7cbc57042d48b233e8381c0f2e7
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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