Hydrochloric Acid → 3-amino-N-[2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-2-fluorobenzamide

HRID 590908Notes

Reaction equation

HRID 590908 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[C:3]=1[NH:22][C:23](=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[C:25]=1[F:33].Cl.[OH-].[Na+]>C(O)C>[NH2:30][C:26]1[C:25]([F:33])=[C:24]([CH:29]=[CH:28][CH:27]=1)[C:23]([NH:22][C:3]1[C:4]([C:18]([F:20])([F:21])[F:19])=[CH:5][C:6]([C:8]([F:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[CH:7][C:2]=1[Br:1])=[O:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86656683N-[2-Bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-2-fluoro-3-nitrobenzamide

Product 1

HCID 866566853-amino-N-[2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-2-fluorobenzamideYield 104.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

0.940 g (1.63 mmol) of N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-nitrobenzamide and 0.960 g (5.05 mmol) of stannous chloride (anhydrous) were added to 10 ml of ethanol, and 1.02 ml (9.78 mmol) of concentrated hydrochloric acid was added thereto, followed by stirring at 60° C. for 4 hours. The reaction mixture was adjusted to pH 10 by the addition of an aqueous sodium hydroxide solution, and the precipitated insolubles were removed by filtration using Celite. The filtrate on Celite was washed with ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic layer was washed with a 20% aqueous sodium hydroxide solution and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=4:1) to prepare 0.930 g (yield 99%) of a target compound.

Workup

  1. additionwas added
  2. customthe precipitated insolubles were removed by filtration
  3. washThe filtrate on Celite was washed with ethyl acetate
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe organic layer was washed with a 20% aqueous sodium hydroxide solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-90704707be7c4e7fb1c6d86d19d63892
Source dataset
uspto-grants-2016_01
Patent number
US09237745B2

Reaction notes

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