Sodium Hydroxide → HCID 10200811, compound

HRID 392779Notes

Reaction equation

HRID 392779 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17](SC)=[CH:16][CH:15]=3)=[N:12][C:11]([C:22]([F:25])([F:24])[F:23])=[N:10]2)=[CH:5][CH:4]=1.[CH:26]1C=C(Cl)C=C(C(OO)=O)C=1.[S:37](S([O-])=O)([O-:39])=[O:38].[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([S:37]([CH3:26])(=[O:39])=[O:38])=[CH:16][CH:15]=3)=[N:12][C:11]([C:22]([F:25])([F:24])[F:23])=[N:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 70297m-Chloroperbenzoic acidHCID 22661020HCID 22661020, compound

Product 1

HCID 10200811HCID 10200811, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-methoxy-phenyl)-5-(4-methylthio-phenyl)-3-trifluoromethyl-1H-1,2,4-triazole (30 g, 0.08 mol) in CH2Cl2 (320 ml) was added portionwise MCPBA (47.2 g, 0.16 mol). The reaction mixture was stirred at room temperature for 1.5 h, then cooled to 0-5° C. and a sodium hydrosulfite solution (500 ml) was carefully added to maintain the temperature below 18-20° C. The pH was adjusted to 8 by the addition of NaOH 30%. The mixture was extracted with dichoromethane, the organic phase was washed with saturated brine, dried over sodium sulfate and evaporated. Flash chromatography on silica gel (toluene/ethyl acetate: 8/2 as the eluent) and recrystallization from ethanol yielded a white solid (29.42 g, 90%) m.p. 156° C.

Workup

  1. temperaturecooled to 0-5° C.
  2. temperatureto maintain the temperature below 18-20° C
  3. extractionThe mixture was extracted with dichoromethane
  4. washthe organic phase was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customFlash chromatography on silica gel (toluene/ethyl acetate: 8/2 as the eluent) and recrystallization from ethanol

Sources & evidence

ORD record
ord-c85048fce965412b9872adb7ffbcde2e
Source dataset
uspto-grants-2004_10
Patent number
US06803380B1

Reaction notes

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