Sodium Thiosulfate → HCID 117974288, compound

HRID 2272903Notes

Reaction equation

HRID 2272903 reaction equation
Cl[C:2]1C=C(C=C[CH:11]=1)C(OO)=[O:6].[CH2:12]([S:14][C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]1[N:32]([CH3:33])[C:23]2=[N:24][CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=[C:22]2[N:21]=1)[CH3:13].C(=O)(O)[O-].[Na+].[S:39]([O-:43])([O-])(=[O:41])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:12]([S:14]([C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]1[N:32]([CH3:33])[C:23]2=[N:24][CH:25]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:27]=[C:22]2[N:21]=1)=[O:6])[CH3:13].[CH2:2]([S:39]([C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]1[N:32]([CH3:33])[C:23]2=[N:24][CH:25]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:27]=[C:22]2[N:21]=1)(=[O:43])=[O:41])[CH3:11]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 117974266HCID 117974266, compound

Product 2

HCID 117974288HCID 117974288, compoundHCID 117974434HCID 117974434, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.25 g of 3-chloroperoxybenzoic acid (69 to 75%) was added to a mixture of 0.25 g of 2-(3-ethylthiothiophen-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine and 5 ml of chloroform, under ice cooling, then the mixture was heated to room temperature and stirred for 1 hour. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were poured to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.10 g of 2-(3-ethylsulfinylthiophen-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (16)) and 0.12 g of 2-(3-ethylsulfonylthiophen-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (17)).

Workup

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

Sources & evidence

ORD record
ord-b39dc9f5c8f543cfb9b024a008d5bb3a
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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