Sodium Thiosulfate → HCID 59200928, compound

HRID 1690157Notes

Reaction equation

HRID 1690157 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([C:12]1[CH:25]=[CH:24][C:15]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=2)=[C:14]([CH2:26][CH2:27][CH3:28])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].ClC1C=CC=[C:34]([C:38]([O:40]O)=[O:39])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CO>[C:38]([O:40][CH2:23][C:19]1[CH:18]=[C:17]([O:16][C:15]2[CH:24]=[CH:25][C:12]([C:3]([O:8][CH2:9][O:10][CH3:11])([C:4]([F:7])([F:6])[F:5])[C:2]([F:1])([F:29])[F:30])=[CH:13][C:14]=2[CH2:26][CH2:27][CH3:28])[CH:22]=[CH:21][N:20]=1)(=[O:39])[CH3:34]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59201058HCID 59201058, compound

Product 1

HCID 59200928HCID 59200928, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-2-methylpyridine (780 mg, 1.78 mmol) in chloroform (2 mL), m-chloroperbenzoic acid (2.05 g) was added at room temperature and the resultant mixture was stirred. After completion of the reaction, the reaction solution was added with an aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate, and then dried using sodium sulfate. After filtration, the filtrate was concentrated in vacuo. The obtained residue was added with acetic anhydride and heated at a surrounding temperature of 140° C. After completion of the reaction, the reaction solution was added with methanol (4 mL) at room temperature, then neutralized by adding a saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (490 mg, yield 56%) was obtained as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. extractiona saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate
  3. customdried
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. additionThe obtained residue was added with acetic anhydride
  7. customAfter completion of the reaction
  8. extractionextracted with ethyl acetate
  9. concentrationconcentrated in vacuo
  10. customThe obtained residue was purified

Sources & evidence

ORD record
ord-e10518dd5ca24b9f8a799c5e25d1dbb0
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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