Potassium Iodide → N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline

HRID 1077900Notes

Reaction equation

HRID 1077900 reaction equation
[F:1][C:2]([F:15])([CH:12]([F:14])[F:13])[CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.Br[CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29].C(=O)(O)[O-].[K+].[I-].[K+]>CN(C)C=O>[C:20]1(=[O:29])[N:19]([CH2:18][CH2:17][NH:9][C:8]2[CH:10]=[CH:11][C:5]([O:4][CH2:3][C:2]([F:15])([F:1])[CH:12]([F:13])[F:14])=[CH:6][CH:7]=2)[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]12

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 516893Potassium BicarbonateHCID 187663254-(2,2,3,3-Tetrafluoropropoxy)aniline

Product 1

HCID 19065098N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)anilineYield 41.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2,2,3,3-tetrafluoropropoxy)aniline (7.4 g), N-(2-bromoethyl)phthalimide (9.0 g), potassium bicarbonate (6.9 g), potassium iodide (5.5 g) and N,N-dimethylformamide (80 ml) are refluxed for 22 hours. The solvent was distilled off under reduced pressure. To the residue, ice-water (200 ml) and ethyl acetate (200 ml) were added and fractionated. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluate; ethyl acetate:hexane=1:2 v/v) and recrystallized from ethyl acetate-diisopropyl ether to give N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline (5.4 g) as white crystals.

Workup

  1. temperatureare refluxed for 22 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionTo the residue, ice-water (200 ml) and ethyl acetate (200 ml) were added
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography (eluate; ethyl acetate:hexane=1:2 v/v)
  8. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-4f949c0669634f73966d4d6bb6abc99b
Source dataset
uspto-grants-1996_08
Patent number
US05545652

Reaction notes

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