Sodium Iodide → N-ethoxycarbonylmethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline

HRID 482048Notes

Reaction equation

HRID 482048 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.Cl[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)(O)[O-].[Na+].[I-].[Na+]>CC(C)=O>[CH2:21]([O:20][C:18]([CH2:17][NH:9][C:8]1[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]=1)=[O:19])[CH3:22]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7751Ethyl chloroacetateHCID 516892Sodium BicarbonateHCID 187663254-(2,2,3,3-Tetrafluoropropoxy)aniline

Product 1

HCID 19065104N-ethoxycarbonylmethyl-4-(2,2,3,3-tetrafluoropropoxy)anilineYield 78.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8.6 g of 4-(2,2,3,3-tetrafluoropropoxy)aniline, 4.8 g of ethyl chloroacetate, 4.8 g of sodium bicarbonate, 3.0 g of sodium iodide and 300 ml of acetone was refluxed for 21 hours. The solvent was distilled off under reduced pressure and 200 ml of ice water and 200 ml of dichloromethane were added to the residue to fractionate. The dichloromethane layer was washed with water, dried over anhydrous magnesium sulfate and distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluted with ethyl acetate:hexane [1:3 v/v]) to give 9.4 g of N-ethoxycarbonylmethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline as pale yellow crystals.

Workup

  1. temperaturewas refluxed for 21 hours
  2. distillationThe solvent was distilled off under reduced pressure and 200 ml of ice water and 200 ml of dichloromethane
  3. additionwere added to the residue
  4. washThe dichloromethane 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 column chromatography (eluted with ethyl acetate:hexane [1:3 v/v])

Sources & evidence

ORD record
ord-8ebfda9ff34640f3a80fea79f747d573
Source dataset
uspto-grants-1998_08
Patent number
US05792780

Reaction notes

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