Water → HCID 86654258, compound

HRID 590935Notes

Reaction equation

HRID 590935 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([C:16]([F:19])([F:18])[F:17])[C:3]=1[NH2:4].[N+:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27])([O-:22])=[O:21].O.C(OCC)(=O)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[C:7]([C:9]([F:14])([F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([C:16]([F:17])([F:18])[F:19])[C:3]=1[NH:4][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8495Benzoyl chloride, 3-nitro-HCID 8857Ethyl AcetateHCID 58297446HCID 58297446, compound

Product 1

HCID 86654258HCID 86654258, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2.50 g (6.99 mmol) of 2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)aniline in 20 ml of pyridine was added 2.72 g (14.7 mmol) of 3-nitrobenzoyl chloride, followed by stirring at 100° C. for 12 hours. To the reaction liquid were added water and ethyl acetate, followed by extraction with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. To the obtained residue were added THF and an aqueous sodium hydroxide solution, followed by stirring at room temperature for 8 hours. The reaction liquid was extracted/dried in the same manner as described above, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=7:1→5:1) to prepare 0.202 g (yield 6%) of a target compound.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with 1 M hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionTo the obtained residue were added THF
  7. stirringby stirring at room temperature for 8 hours
  8. customThe reaction liquid
  9. customwas extracted/dried in the same manner
  10. customwas evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=7:1→5:1)

Sources & evidence

ORD record
ord-e2e102b2527344a3933a059c4827abb0
Source dataset
uspto-grants-2016_01
Patent number
US09237745B2

Reaction notes

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