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

HRID 2094235Notes

Reaction equation

HRID 2094235 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-872097ab47f1492a87072454e86a43b4
Source dataset
uspto-grants-2013_05
Patent number
US08445519B2

Reaction notes

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