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

HRID 418702Notes

Reaction equation

HRID 418702 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-5ef65c5594cc48b3b4e2032fb938c161
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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