Sodium Thiosulfate → HCID 67396289, compound

HRID 70503Notes

Reaction equation

HRID 70503 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]1([C:15]2[CH:16]=[CH:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:19][CH:20]=2)[CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH:12]1([C:15]2[CH:20]=[N+:19]([O-:9])[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67396867Ethyl 5-cyclopropylpyridine-2-carboxylate

Product 1

HCID 67396289HCID 67396289, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

m-Chloroperbenzoic acid (55 g) was added to a solution of ethyl 5-cyclopropylpyridine-2-carboxylate (15.5 g) in chloroform (300 mL) under ice-cooling, and the mixture was stirred at room temperature for four hours. The reaction solution was poured into a mixed solvent of saturated aqueous sodium bicarbonate and a saturated sodium thiosulfate solution, and the mixture was stirred at room temperature for 30 minutes. After extraction with chloroform, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give ethyl 5-cyclopropylpyridine-2-carboxylate 1-oxide (15.4 g) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. extractionAfter extraction with chloroform
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

Sources & evidence

ORD record
ord-0e8ae53d7f774878a6138498925962be
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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