Aniline → Aniline, N-(2,2,2-trifluoroethyl)-

HRID 1640234Notes

Reaction equation

HRID 1640234 reaction equation
FC(F)(F)S(O[CH2:7][C:8]([F:11])([F:10])[F:9])(=O)=O.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C(C)=CC=CC=1>[F:9][C:8]([F:11])([F:10])[CH2:7][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 9596Aniline, N-(2,2,2-trifluoroethyl)-

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.5 g (10.7 mmol) 2,2,2-trifluoroethyl trifluoromethanesulphonate were added to 2.0 g (21.5 mmol) aniline in 50 mL xylene and the mixture was refluxed for 2 days. After cooling, the mixture was filtered, washed with DIPE and the filtrate was evaporated down i.vac. The residue was purified by flash chromatography. The product fractions were combined and evaporated down i.vac.

Workup

  1. temperaturethe mixture was refluxed for 2 days
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washwashed with DIPE
  5. customthe filtrate was evaporated down i.vac
  6. customThe residue was purified by flash chromatography
  7. customevaporated down i.vac

Sources & evidence

ORD record
ord-1e0a5ea719cf40c5a311b798f7ce4fb7
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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