4-Chloroaniline → 4-chloro-N-(2-benzyloxyethyl)aniline

HRID 359078Notes

Reaction equation

HRID 359078 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH2:9]([O:16][CH2:17][CH2:18]OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:18][CH2:17][O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 516892Sodium Bicarbonate2×HCID 108572722-Benzyloxyethyl mesylate

Product 1

HCID 150865894-chloro-N-(2-benzyloxyethyl)anilineYield 33.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

p-Chloroaniline (8 g), methanesulfonic acid 2-benzyloxyethyl ester (12.29 g) and sodium hydrogen carbonate (hereinafter, reffered to as sodium bicarbonate) (8.97 g) were dissolved in dioxane (35 ml), suspended and the mixture was heated with stirring for 24 hours. After concentrated under reduced pressure, water and ethyl acetate were added to the mixture and the mixture was separated into layers. The organic layer was washed with water 2 times, and concentrated again under reduced pressure, and the resulting rsidue was subjected to column chromatography on silica gel, and eluted with chloroform/n-hexane [2:1 (v/v)] to give 4-chloro-N-(2-benzyloxyethyl)aniline (4.63 g).

Workup

  1. temperaturethe mixture was heated
  2. concentrationAfter concentrated under reduced pressure, water and ethyl acetate
  3. additionwere added to the mixture
  4. customthe mixture was separated into layers
  5. washThe organic layer was washed with water 2 times
  6. concentrationconcentrated again under reduced pressure
  7. washeluted with chloroform/n-hexane [2:1 (v/v)]

Sources & evidence

ORD record
ord-2523b2115e024f6f8902a8b073307a59
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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