Sodium Thiosulfate → HCID 117974412, compound

HRID 2272901Notes

Reaction equation

HRID 2272901 reaction equation
Cl[C:2]1C=C(C=C[CH:11]=1)C(OO)=O.C(S[C:15]1[S:16][CH:17]=[CH:18][C:19]=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)C.C(=O)(O)[O-].[Na+].[S:39]([O-:43])([O-])(=[O:41])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:39]([C:15]1[S:16][CH:17]=[CH:18][C:19]=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

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 117974188HCID 117974188, compound

Product 1

HCID 117974412HCID 117974412, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.20 g of 3-chloroperoxybenzoic acid (69 to 75%) was added to a mixture of 0.20 g of 2-(2-ethylthiothiophen-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine and 3 ml of chloroform, under ice cooling, and the mixture was heated to room temperature and stirred for 2 hours. 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 0.20 g of 2-(2-ethylsulfonylthiophen-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (14)).

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-31ea15cd8653403dbdc1a0000656ecce
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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