Sodium Hydroxide → 3-(3,5-Difluoro-phenyl)-5-methanesulfonyl-4-methyl-4H-[1,2,4]triazole

HRID 639835Notes

Reaction equation

HRID 639835 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:14]=[C:15]([C:20]2[N:24]([CH3:25])[C:23]([S:26][CH3:27])=[N:22][N:21]=2)[CH:16]=[C:17]([F:19])[CH:18]=1.[OH-:28].[Na+]>C(Cl)Cl>[F:12][C:13]1[CH:14]=[C:15]([C:20]2[N:24]([CH3:25])[C:23]([S:26]([CH3:27])(=[O:9])=[O:28])=[N:22][N:21]=2)[CH:16]=[C:17]([F:19])[CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 578379693-(3,5-difluorophenyl)-4-methyl-5-(methylthio)-4H-1,2,4-triazole

Product 1

HCID 578380053-(3,5-Difluoro-phenyl)-5-methanesulfonyl-4-methyl-4H-[1,2,4]triazoleYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-CPBA (10 g, 33-50 mmol, 57-86% pure) was added to a solution of 3-(3,5-difluorophenyl)-4-methyl-5-(methylthio)-4H-1,2,4-triazole (4.9 g, 20.3 mmol) in DCM (60 mL) and the reaction was stirred o.n. 2M NaOH (50 mL) was added and the mixture was extracted. The water phase was re-extracted with EtOAc (2×) and the combined organic phases were dried (MgSO4) and evaporated to give 5.4 g (98%) of the title compound.

Workup

  1. extractionthe mixture was extracted
  2. extractionThe water phase was re-extracted with EtOAc (2×)
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-a0ab7f550d1e4c17a322af2e5fede6fe
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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