2-Bromoaniline → N-(2-bromo-phenyl)-3-ethoxy-acrylamide

HRID 2415889Notes

Reaction equation

HRID 2415889 reaction equation
[CH2:1]([O:3][CH:4]=[CH:5][C:6](Cl)=[O:7])[CH3:2].[Br:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12]>N1C=CC=CC=1>[Br:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][C:6](=[O:7])[CH:5]=[CH:4][O:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 119922-BromoanilineHCID 30144293-Ethoxy-2-propenoyl chloride

Product 1

HCID 68586854N-(2-bromo-phenyl)-3-ethoxy-acrylamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

10 g (74.31 mmol) of 3-ethoxy-acryloyl-chloride are added dropwise at 0° C. to a solution of 11.6 g (67.43 mmol) of 2-bromo-aniline in 60 ml of pyridine and stirred for one hour at this temperature. The mixture is allowed to come up to ambient temperature and stirred for two hours. Then the reaction mixture is extracted with water and ethyl acetate. The organic phase is extracted with water and 1 N hydrochloric acid, combined with activated charcoal and dried over sodium sulphate. The solvent is distilled off and the residue is recrystallised from isopropanol/water 2:1.

Workup

  1. customto come up to ambient temperature
  2. stirringstirred for two hours
  3. extractionThen the reaction mixture is extracted with water and ethyl acetate
  4. extractionThe organic phase is extracted with water and 1 N hydrochloric acid
  5. dry with materialdried over sodium sulphate
  6. distillationThe solvent is distilled off
  7. customthe residue is recrystallised from isopropanol/water 2:1

Sources & evidence

ORD record
ord-5994f245d8a74041b438cb251581ac32
Source dataset
uspto-grants-2004_11
Patent number
US06821967B2

Reaction notes

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