2-Chloroethanol → N-(2-hydroxyethyl)-3-chloroaniline

HRID 971846Notes

Reaction equation

HRID 971846 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH2:9](Cl)[CH2:10][OH:11].C(=O)([O-])[O-].[Na+].[Na+]>>[OH:11][CH2:10][CH2:9][NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 3

HCID 342-ChloroethanolHCID 79323-ChloroanilineHCID 10340Sodium Carbonate

Product 1

HCID 12296176N-(2-hydroxyethyl)-3-chloroaniline

Procedure

A mixture consisting of 50.8 gm of 3-chloro-aniline, 36 gm of ethylenechlorohydrin and 50 gm of anhydrous sodium carbonate was refluxed for four hours, while stirring. Thereafter, the reaction mixture was suction-filtered while still hot, and the filter cake was washed with ethyl acetate. The filtrate was then distilled in vacuo; the desired product passed over at 182° C./14 mm Hg.

Workup

  1. temperaturewas refluxed for four hours
  2. filtrationThereafter, the reaction mixture was suction-filtered while still hot, and the filter cake
  3. washwas washed with ethyl acetate
  4. distillationThe filtrate was then distilled in vacuo
  5. custompassed over at 182° C./14 mm Hg

Sources & evidence

ORD record
ord-9ca4480728ae4a4eb7c3c9b09fc412b1
Source dataset
uspto-grants-1979_07
Patent number
US04161528

Reaction notes

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