1h-1,2,4-Triazole sodium salt → 4-[[2-(1h-1,2,4-Triazol-1-yl)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173513Notes

Reaction equation

HRID 1173513 reaction equation
CS(O[CH2:6][CH2:7][N:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=1)[CH2:9][C:10]([F:13])([F:12])[F:11])(=O)=O.[Na].[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1>CN(C=O)C>[N:27]1([CH2:6][CH2:7][N:8]([CH2:9][C:10]([F:13])([F:12])[F:11])[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=2)[CH:31]=[N:30][CH:29]=[N:28]1

Participants

4

Reactant 2

HCID 454898221h-1,2,4-Triazole sodium saltHCID 866237322-[[4-Cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl methanesulfonate

Product 1

HCID 875240344-[[2-(1h-1,2,4-Triazol-1-yl)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl methanesulfonate, Example 15C (0.050 g, 0.128 mmol) and 1,2,4-triazole sodium salt (0.023 g, 0.256 mmol) in DMF (2 mL) was heated at 60° C. under N2 for 45 min. Upon cooling, the mixture was partitioned between Et2O and water. The organic phase was washed with water and the combined aqueous phases were extracted twice with Et2O. The combined organic phases were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel chromatography (5-80% EtOAc/hexanes gradient followed by 1-10% MeOH/EtOAc gradient) and the product was crystallized from CH2Cl2/hexanes to give the title compound as a white solid (0.038 mg, 83% yield): MS (ES) m/z 364 (M+1).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between Et2O and water
  3. washThe organic phase was washed with water
  4. extractionthe combined aqueous phases were extracted twice with Et2O
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (5-80% EtOAc/hexanes gradient followed by 1-10% MeOH/EtOAc gradient)
  9. customthe product was crystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-1e6b7ba03a114ff3b4beaf79598b3c67
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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