4-(Trifluoromethyl)aniline → HCID 67236836, compound

HRID 1470963Notes

Reaction equation

HRID 1470963 reaction equation
CS(O[CH:6]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)(=O)=O.[F:29][C:30]([F:39])([F:38])[C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>CN(C=O)C>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C@@H:9]2[CH2:8][CH2:7][C@@H:6]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[N:35]2[C:34]2[CH:36]=[CH:37][C:31]([C:30]([F:29])([F:38])[F:39])=[CH:32][CH:33]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 582265311,4-Bis(4-bromophenyl)butane-1,4-diyl dimethanesulfonate

Product 1

HCID 67236836HCID 67236836, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The product from Example 42B (11.13 g, 20.0 mmol) and 4-(trifluoromethyl)aniline (32.2 g, 200 mmol) were combined in DMF (50 mL). The mixture was stirred at 50° C. under nitrogen overnight. The reaction mixture was evaporated and the residue was diluted with ethyl acetate, treated with 1M HCl, stirred for 10 minutes, and filtered to remove the solid. The organic layer of filtrate was washed with brine, dried with sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (0 to 1%). The title compounds (500 mg, 5%) were eluted as the first of 2 stereoisomers and were obtained as a mixture of trans diastereomers.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with ethyl acetate
  3. additiontreated with 1M HCl
  4. stirringstirred for 10 minutes
  5. filtrationfiltered
  6. customto remove the solid
  7. washThe organic layer of filtrate was washed with brine
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (0 to 1%)
  12. washThe title compounds (500 mg, 5%) were eluted as the first of 2 stereoisomers
  13. customwere obtained as a mixture of trans diastereomers

Sources & evidence

ORD record
ord-b634bd9ca0da468f8d827df0d6bb7d5f
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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