2-(Trifluoromethyl)aniline → HCID 18541890, compound

HRID 590934Notes

Reaction equation

HRID 590934 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+].[F:14][C:15]([F:24])([F:23])[C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18].[F:25][C:26](I)([F:31])[C:27]([F:30])([F:29])[F:28]>CN(C=O)C.C(OCC)(=O)C.O>[F:25][C:26]([F:31])([C:21]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([C:15]([F:23])([F:24])[F:14])[CH:22]=1)[C:27]([F:30])([F:29])[F:28]

Participants

8

Reactant 4

HCID 69222-(Trifluoromethyl)anilineHCID 9636Iodopentafluoroethane2×HCID 24489Sodium DithioniteHCID 516892Sodium Bicarbonate

Product 1

HCID 18541890HCID 18541890, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

To 40 ml of an aqueous solution of 7.04 g (40.4 mmol) of 85% sodium hydrosulfite and 3.40 g (40.4 mmol) of sodium hydrogen carbonate were added 13.6 g (33.7 mmol) of 2-(trifluoromethyl)aniline and 40 ml of DMF. To this reaction liquid was added 50 ml of a solution of 11.2 g (45.5 mmol) of 1,1,2,2,2-pentafluoroethyliodide in DMF (DMF was cooled to −30° C., and 1,1,2,2,2-pentafluoroethyl iodide was dissolved therein), and placed in an autoclave, followed by stirring at 110° C. for 9 hours. After being left to stand at room temperature overnight, water and ethyl acetate were added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=10:1→5:1) to prepare 1.95 g (yield 21%) of a target compound.

Workup

  1. customTo this reaction liquid
  2. waitAfter being left
  3. waitto stand at room temperature overnight
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialThe organic layer was dried over anhydrous sodium 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=10:1→5:1)

Sources & evidence

ORD record
ord-b1caca2c84344e0b9de7748bc5614d27
Source dataset
uspto-grants-2016_01
Patent number
US09237745B2

Reaction notes

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