Ethyl Acetate → HCID 18476298, compound

HRID 2187658Notes

Reaction equation

HRID 2187658 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[CH3:13][C:14]1[CH:23]=[CH:22][C:17]([C:18](=O)[CH2:19]Br)=[CH:16][CH:15]=1.C(OCC)(=O)C>C(N(CC)C1C=CC=CC=1)C.C1(C)C(C)=CC=CC=1>[CH3:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]2[NH:8][C:7]3[C:9]([CH:19]=2)=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=3)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 692722-Bromo-4'-methylacetophenoneHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 18476298HCID 18476298, compound

Reagents, catalysts & solvents 2

HCID 7061N,N-DiethylanilineSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
165 °C

Procedure

To a stirred solution of 5.3 g (30 mmol) of 4-trifluoromethoxyaniline in 8 ml of N,N-diethylaniline was added dropwise at 165° C. a solution of 4.3 g of 4-methylphenacyl bromide in 7.5 ml of xylene. It was heated at 165° C. for 3 h. The mixture was cooled followed by addition of 50 ml of ethyl acetate. It was washed with 2N hydrochloric acid, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified via repeated column chromatography on silica gel using a hexane dichloromethane gradient (100:0 to 50:50). The title compound thus obtained was recrystallized from hexane.

Workup

  1. temperatureThe mixture was cooled
  2. washIt was washed with 2N hydrochloric acid
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-eede3d8a353b4546b4af70361fda20d9
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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