Sodium Thiosulfate → HCID 117974507, compound

HRID 2272907Notes

Reaction equation

HRID 2272907 reaction equation
Cl[C:2]1C=C(C=C[CH:11]=1)C(OO)=O.C(S[C:15]1[N:16]([C:20]2[N:32]([CH3:33])[C:23]3=[N:24][CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=[C:22]3[N:21]=2)[CH:17]=[CH:18][CH:19]=1)C.[S:34]([O-:38])([O-])(=[O:36])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:34]([C:15]1[N:16]([C:20]2[N:32]([CH3:33])[C:23]3=[N:24][CH:25]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:27]=[C:22]3[N:21]=2)[CH:17]=[CH:18][CH:19]=1)(=[O:38])=[O:36])[CH3:11]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 117974191HCID 117974191, compound

Product 1

HCID 117974507HCID 117974507, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.5 g of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 0.32 g of 2-(2-ethylthiopyrrol-1-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine and 8 ml of chloroform, under ice cooling, and the mixture was stirred at room temperature for 3 hours and then allowed to stand overnight at room temperature. A 10% aqueous sodium thiosulfate solution was poured 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, then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.33 g of 2-(2-ethylsulfonylpyrrol-1-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (24)).

Workup

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

Sources & evidence

ORD record
ord-2f89a66bffe6492d80c54bd5126eb804
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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