Aniline → N-(1-ethoxy-2,2,2-trifluoroethyl)aniline

HRID 2193763Notes

Reaction equation

HRID 2193763 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][CH:11](O)[C:12]([F:15])([F:14])[F:13])[CH3:9]>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:8]([O:10][CH:11]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]([F:15])([F:14])[F:13])[CH3:9]

Participants

5

Reactant 2

HCID 6115AnilineHCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-

Product 1

HCID 12990236N-(1-ethoxy-2,2,2-trifluoroethyl)anilineYield 86.7%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 702EthanolSolvent

Procedure

A solution of aniline (2 mL, 21.9 mmol), trifluoroacetaldehyde ethyl hemiacetal (2.6 mL, 21.9 mmol) and p-toluenesulfonic acid monohydrate (220 mg, 1.16 mmol) in ethanol (25 mL) was heated to reflux for 3 h under continuous stirring. The reaction mixture was cooled, the solvent was removed under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to afford title compound 325 (4.16 g, crude) as a yellow oil which was used directly for the next step.

Workup

  1. temperatureto reflux for 3 h under continuous stirring
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c3023dd08b4a44a39e8234e5482dea78
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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