Sodium Thiosulfate → HCID 117974341, compound

HRID 2272904Notes

Reaction equation

HRID 2272904 reaction equation
Cl[C:2]1C=C(C=C[CH:11]=1)C(OO)=[O:6].[CH2:12]([S:14][C:15]1[C: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][S:18][CH:19]=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[C: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][S:18][CH:19]=1)=[O:6])[CH3:13].[CH2:2]([S:39]([C:15]1[C: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][S:18][CH:19]=1)(=[O:43])=[O:41])[CH3:11]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 117974164HCID 117974164, compound

Product 2

HCID 117974341HCID 117974341, compoundHCID 117974360HCID 117974360, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.02 g of 3-chloroperoxybenzoic acid (69 to 75%) was added to a mixture of 1.01 g of 2-(4-ethylthiothiophen-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine and 10 ml of chloroform, under ice cooling, then the mixture was heated to room temperature and stirred for 3 hours. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were poured into 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 0.51 g of 2-(4-ethylsulfinylthiophen-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (19)) and 0.52 g of 2-(4-ethylsulfonylthiophen-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (20)).

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-ef0b28f988904eb79f45ba88cde9047d
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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