3-Fluoroaniline → HCID 18442670, compound

HRID 458648Notes

Reaction equation

HRID 458648 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Br[CH2:10][C:11]([NH2:13])=[O:12]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:10][C:11]([NH2:13])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 97423-FluoroanilineHCID 696322-Bromoacetamide

Product 1

HCID 18442670HCID 18442670, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution (50 ml) of 1.45 ml of 3-fluoroaniline and 1.37 g of 2-bromoacetamide was heated under reflux for 24 hours. The reaction liquid was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in chloroform and washed with 1N aqueous sodium hydroxide solution. The aqueous solution used for the washing was extracted with chloroform and combined with the earlier obtained chloroform extract, dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was separated and purified on silica gel column chromatography (chloroform/methanol=100/3) to provide 1.03 g of the title compound as a pale yellow solid.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe reaction liquid
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with 1N aqueous sodium hydroxide solution
  6. extractionwas extracted with chloroform
  7. customearlier obtained chloroform
  8. extractionextract
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off
  11. customThe residue was separated
  12. custompurified on silica gel column chromatography (chloroform/methanol=100/3)

Sources & evidence

ORD record
ord-f268feccb04947bfa8c8c2a4cb0c0c63
Source dataset
uspto-grants-2007_03
Patent number
US07192964B2

Reaction notes

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