Sodium Thiosulfate → 3-(5-Isopropyl-2,4-bis-methoxymethoxyphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-5-methanesulfonyl-[1,2,4]triazole

HRID 1947210Notes

Reaction equation

HRID 1947210 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[CH:12]([C:15]1[C:16]([O:46][CH2:47][O:48][CH3:49])=[CH:17][C:18]([O:42][CH2:43][O:44][CH3:45])=[C:19]([C:21]2[N:25]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][N:33]4[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]4)=[CH:28][CH:27]=3)[C:24](SC)=[N:23][N:22]=2)[CH:20]=1)([CH3:14])[CH3:13].[S:50]([O-:54])([O-])(=[O:52])=S.[Na+].[Na+].S(=O)(O)[O-].[K+].C(=O)([O-])O.[Na+]>C(OCC)C.C(Cl)Cl>[CH:12]([C:15]1[C:16]([O:46][CH2:47][O:48][CH3:49])=[CH:17][C:18]([O:42][CH2:43][O:44][CH3:45])=[C:19]([C:21]2[N:25]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][N:33]4[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38]4)=[CH:28][CH:27]=3)[C:24]([S:50]([CH3:2])(=[O:54])=[O:52])=[N:23][N:22]=2)[CH:20]=1)([CH3:13])[CH3:14]

Participants

8

Reactant 5

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 23663620Potassium BisulfiteHCID 598299083-(5-Isopropyl-2,4-bis-methoxymethoxyphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-5-methylsulfanyl-[1,2,4]triazole

Product 1

HCID 598298563-(5-Isopropyl-2,4-bis-methoxymethoxyphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-5-methanesulfonyl-[1,2,4]triazoleYield 50%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3-chloroperbenzoic acid (3.91 g, 22.7 mmol) was added to a methylene chloride (9 mL) solution of 3-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-5-methylsulfanyl-[1,2,4]triazole (F652-07, 2.05 g, 3.78 mmol). After stirring at room temperature for 9.5 hours, additional 3-chloroperbenzoic acid (717 mg, 4.15 mmol) was added and stirring was continued overnight. After cooling to ice cold, saturated aqueous sodium thiosulfate and then 10% aqueous potassium bisulfite were added, and stirring was continued for a while. Further, saturated aqueous sodium hydrogencarbonate was added and the mixture was stirred, and then extracted with chloroform. The extract was washed sequentially with saturated aqueous sodium hydrogencarbonate, water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filtration and evaporation gave pale brown foam. After adding diethyl ether, the insoluble solids were removed by filtration, and the solvent in the filtrate was distilled off under reduced pressure. The solids thus obtained were purified by silica gel column chromatography (chloroform, methanol) to obtain 3-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-5-methanesulfonyl-[1,2,4]triazole (F652-08, pale yellow foam, 1.08 g, 50%).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. stirringstirring
  4. stirringthe mixture was stirred
  5. extractionextracted with chloroform
  6. washThe extract was washed sequentially with saturated aqueous sodium hydrogencarbonate, water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationFiltration and evaporation
  9. customgave pale brown foam
  10. customthe insoluble solids were removed by filtration
  11. distillationthe solvent in the filtrate was distilled off under reduced pressure
  12. customThe solids thus obtained
  13. customwere purified by silica gel column chromatography (chloroform, methanol)

Sources & evidence

ORD record
ord-95acb43618f342fbb4b5571b99e5bbf7
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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