Imidazole → HCID 728760, compound

HRID 1893432Notes

Reaction equation

HRID 1893432 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(C(C)C)CC)(C)C.[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>C(#N)C>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 677784-Fluoro-3-nitrobenzotrifluoride2×HCID 81531Diisopropylethylamine

Product 1

HCID 728760HCID 728760, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (15.00 g; 71.8 mmol; 1 eq) and diisopropylethylamine (12.5 mL; 71.8 mmol; 1 eq) in anhydrous acetonitrile (650 mL), imidazole (4.88 g; 71.8 mmol; 1 eq) is added under argon. The reaction mixture is allowed to stir under reflux for 20 hours until 1-fluoro-2-nitro-4-(trifluoromethyl)benzene has completely reacted. The crude mixture is concentrated under vacuum and the resulting powder dissolved in ethyl acetate (250 mL). The organic phase is then washed with water (100 mL), brine (100 mL) and dried over sodium sulfate to provide an orange powder after concentration under vacuum. Further purification by flash chromatography on silica gel (ethyl acetate/cyclohexane 5:5) afforded the title compound (17.7 g; 68.5 mmol; 96%) as a brown powder.

Workup

  1. customhas completely reacted
  2. concentrationThe crude mixture is concentrated under vacuum
  3. dissolutionthe resulting powder dissolved in ethyl acetate (250 mL)
  4. washThe organic phase is then washed with water (100 mL), brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. customto provide an orange powder
  7. concentrationafter concentration under vacuum
  8. customFurther purification by flash chromatography on silica gel (ethyl acetate/cyclohexane 5:5)

Sources & evidence

ORD record
ord-d413cb14209642b89a42300d556d9723
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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