Acetonitrile → HCID 59820929, compound

HRID 1363664Notes

Reaction equation

HRID 1363664 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[CH:7]=1.[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[CH2:22]([N:24]([CH2:25][CH3:26])[C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[CH:7]=1)[CH3:23]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 59820885HCID 59820885, compound

Product 1

HCID 59820929HCID 59820929, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-fluoro-2-nitro-4′-(trifluoromethoxy)biphenyl (compound of Example 78(1)) (700 mg, 2.32 mmol), diethylamine (339 mg, 4.64 mmol), potassium carbonate (320 mg, 2.32 mmol) and acetonitrile (5 ml) was stirred at 100° for 10 hours under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1) to give the title compound (580 mg, 70.5%) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-3114de93395b4c16ad0ee9c06d968089
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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