Acetonitrile--water (1/1) → HCID 24785733, compound

HRID 523458Notes

Reaction equation

HRID 523458 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]([C:9]1[C:13]([S:14][C:15]([F:18])([F:17])[F:16])=[C:12]([CH3:19])[N:11]([C:20]2[C:25]([Cl:26])=[CH:24][C:23]([C:27]([F:30])([F:29])[F:28])=[CH:22][C:21]=2[Cl:31])[N:10]=1)#[N:8].C(#N)C.[OH2:35]>C(OCC)(=O)C.[Ru](Cl)(Cl)Cl>[C:7]([C:9]1[C:13]([S:14]([C:15]([F:17])([F:16])[F:18])(=[O:2])=[O:35])=[C:12]([CH3:19])[N:11]([C:20]2[C:25]([Cl:26])=[CH:24][C:23]([C:27]([F:29])([F:30])[F:28])=[CH:22][C:21]=2[Cl:31])[N:10]=1)#[N:8]

Participants

6

Reactant 3

HCID 18373917Acetonitrile--water (1/1)HCID 23667635Sodium periodateHCID 24785465HCID 24785465, compound

Product 1

HCID 24785733HCID 24785733, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Sodium periodate (20 mg) and ruthenium chloride (3 mg) were added to a solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methyl-4-trifluoromethylthiopyrazole (100 mg), that is described in Example 1, in a mixture of acetonitrile-water (4:1). The reaction mixture was stirred overnight whereupon the mixture was diluted with ethyl acetate and filtered over silica gel. The organic filtrate was washed with water, dried over anhydrous magnesium sulfate, filtered over Celite and concentrated under reduced pressure to give the title compound as a white solid (73 mg, 68%). MS (ES): M/Z [M+H]=452. 1H NMR: (400 MHz, DMSO-d6): 2.46 (s, 3H) and 7.87 (s, 2H). 19F NMR (376 MHz, DMSO-d6): −63.77 (s, 3F) and −79.83 (s, 3F).

Workup

  1. filtrationfiltered over silica gel
  2. washThe organic filtrate was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered over Celite
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3351322f15845a0af28f6acac117f30
Source dataset
uspto-grants-2016_05
Patent number
US09339033B2

Reaction notes

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