Sodium Thiosulfate → HCID 59829848, compound

HRID 1947216Notes

Reaction equation

HRID 1947216 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[CH:12]([N:15]1[C:19](SC)=[N:18][N:17]=[C:16]1[C:22]1[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[C:25]([O:31][CH2:32][O:33][CH3:34])=[CH:24][C:23]=1[O:35][CH2:36][O:37][CH3:38])([CH3:14])[CH3:13].[S:39]([O-:43])([O-])(=[O:41])=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH:12]([N:15]1[C:19]([S:39]([CH3:2])(=[O:43])=[O:41])=[N:18][N:17]=[C:16]1[C:22]1[CH:27]=[C:26]([CH:28]([CH3:29])[CH3:30])[C:25]([O:31][CH2:32][O:33][CH3:34])=[CH:24][C:23]=1[O:35][CH2:36][O:37][CH3:38])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59829798HCID 59829798, compound

Product 1

HCID 59829848HCID 59829848, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While stirring in ice cold conditions, 3-chloroperbenzoic acid (4.20 g, 24.4 mmol) was added to a methylene chloride (10 mL) solution of 4-isopropyl-3-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-5-methylsulfanyl-4H-[1,2,4]triazole (F63-04, 1.93 g, 4.87 mmol). After stirring at room temperature for 2 hours, the mixture was bring back to ice cold conditions again, and saturated aqueous sodium thiosulfate and then saturated aqueous sodium hydrogencarbonate were added. After stirring for a while, the reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated sodium chloride solution. After drying the extract over anhydrous sodium, sodium sulfate was removed by filtration and the solvent was distilled off under reduced pressure to obtain a pale yellow foam. After purification by silica gel column chromatography (hexane, ethyl acetate), 4-isopropyl-3-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-5-methylsulfonyl-4H-[1,2,4]triazole (F63-05, colorless foam, 1.65 g, 79%) was obtained.

Workup

  1. stirringAfter stirring for a while
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated sodium chloride solution
  4. customAfter drying the
  5. extractionextract over anhydrous sodium, sodium sulfate
  6. customwas removed by filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain a pale yellow foam
  9. customAfter purification by silica gel column chromatography (hexane, ethyl acetate)

Sources & evidence

ORD record
ord-4968977727da4271869e66f1097c2479
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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