4-(Trifluoromethyl)aniline → HCID 69201865, compound

HRID 898825Notes

Reaction equation

HRID 898825 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[C:12]([N:18]1[CH2:22][CH2:21][O:20][C:19]1=[O:23])(=[O:17])[CH:13]=[CH:14][CH2:15][CH3:16].[Cl-].[NH4+]>C1(C)C=CC=CC=1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][CH:14]([CH2:15][CH3:16])[CH2:13][C:12]([N:18]2[CH2:22][CH2:21][O:20][C:19]2=[O:23])=[O:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 99644-(Trifluoromethyl)anilineHCID 25517Ammonium ChlorideHCID 69200777HCID 69200777, compound

Product 1

HCID 69201865HCID 69201865, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-trifluoromethylaniline (193 mg, 1.2 mmol) and 3-(2-pentenoyl)-1,3-oxazolidin-2-one (189 mg, 1.0 mmol) in toluene (3 ml) in a stream of nitrogen was added Pd((R)-binap)(H2O)2(OTf)2 (26.6 mg, 0.025 mmol), and the resulting mixture was stirred at room temperature for 16 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride (10 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate (10 ml). The organic layer was dried over anhydrous magnesium sulfate. The solvent was then evaporated off and the crude product obtained was purified by a silica gel column chromatography (hexane:ethyl acetate=1:1) to give the objective compound 3-[3-(4-trifluoromethylanilino)pentanoyl]-1,3-oxazolidin-2-one (165 mg, 50% yield). Enantiomeric excess ratio of this product was determined by a liquid chromatography using a column for separation of optical isomers (column: OA-2000) to be 70% e.e.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate (10 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was then evaporated off
  5. customthe crude product obtained
  6. customwas purified by a silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-fdc4f6473c26412cbf136a15dc8244f1
Source dataset
uspto-grants-2008_04
Patent number
US07351849B2

Reaction notes

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