Trifluoroacetic acid → HCID 19038490, compound

HRID 263531Notes

Reaction equation

HRID 263531 reaction equation
F[C:2](F)(F)C(O)=O.[C:8]([C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=2)[NH2:18])=[CH:12][CH:11]=1)#[N:9]>ClCCl>[C:8]([C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=2)[NH:18][CH3:2])=[CH:12][CH:11]=1)#[N:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 45701454-(3-Aminophenoxy)benzonitrile

Product 1

HCID 19038490HCID 19038490, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous trifluoroacetic acid (20 ml) was added to 20 ml of dichloromethane solution containing 1.53 g of 3-(4-cyanophenoxy)aniline, and the reaction mixture was stirred for 30 minutes at room temperature. The solvent was evaporated under a reduced pressure, and the thus obtained residue was dissolved in 40 ml of 2-butanone. Then, 3.14 g of methyl iodide and 2.09 g of potassium carbonate were added thereto. The reaction mixture was heated for 3 hours under reflux, insoluble materials were separated by filtration, and the solvent was evaporated under a reduced pressure. To the thus obtained residue were added 30 ml of methanol, 20 ml of water and 1.10 g of potassium carbonate. The reaction mixture was heated for 2 hours under reflux, diluted with water and then extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluant; hexane:ethyl acetate=2:1) to obtain 1.52 g of 3-(4-cyanophenoxy)-N-methylaniline.

Workup

  1. customThe solvent was evaporated under a reduced pressure
  2. dissolutionthe thus obtained residue was dissolved in 40 ml of 2-butanone
  3. additionThen, 3.14 g of methyl iodide and 2.09 g of potassium carbonate were added
  4. temperatureThe reaction mixture was heated for 3 hours
  5. temperatureunder reflux
  6. custominsoluble materials were separated by filtration
  7. customthe solvent was evaporated under a reduced pressure
  8. additionTo the thus obtained residue were added 30 ml of methanol, 20 ml of water and 1.10 g of potassium carbonate
  9. temperatureThe reaction mixture was heated for 2 hours
  10. temperatureunder reflux
  11. additiondiluted with water
  12. extractionextracted with ethyl acetate
  13. washThe organic layer was washed with saturated sodium chloride aqueous solution
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customThe solvent was evaporated under a reduced pressure
  16. customthe resulting residue was purified by silica gel column chromatography (eluant; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c705bfaadecc496eae5a7a2630410a87
Source dataset
uspto-grants-1997_07
Patent number
US05643931

Reaction notes

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