4-(Trifluoromethyl)aniline → HCID 11301521, compound

HRID 898823Notes

Reaction equation

HRID 898823 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:17]1[CH2:21][CH2:20][O:19][C:18]1=[O:22])(=[O:16])/[CH:13]=[CH:14]/[CH3:15].[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]([CH3:15])[CH2:13][C:12]([N:17]2[CH2:21][CH2:20][O:19][C:18]2=[O:22])=[O:16])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 99644-(Trifluoromethyl)anilineHCID 25517Ammonium ChlorideHCID 5365845HCID 5365845, compound

Product 1

HCID 11301521HCID 11301521, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-trifluoromethylaniline (193 mg, 1.2 mmol) and 3-crotonoyl-1,3-oxazolidin-2-one (155 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 resulting 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-(4-trifluoromethylanilino)butyryl-1,3-oxazolidin-2-one (238 mg, 75% yield). Enantiomeric excess ratio of this product was determined by a liquid chromatography using a column for separation of optical isomers (column: AD-H) to be 83% e.e.

Workup

  1. customAfter completion of the reaction
  2. extractionthe resulting 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-c2539e421c084425899c51982ee7f755
Source dataset
uspto-grants-2008_04
Patent number
US07351849B2

Reaction notes

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