Ethylamine → (2E)-3-(3-Bromophenyl)-N-ethyl-2-propenamide

HRID 372479Notes

Reaction equation

HRID 372479 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7](Cl)=[O:8].[CH2:13]([NH2:15])[CH3:14]>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([NH:15][CH2:13][CH3:14])=[O:8]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 14959106trans 3-Bromocinnamoyl chloride

Product 1

HCID 688145(2E)-3-(3-Bromophenyl)-N-ethyl-2-propenamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of trans 3-bromocinnamoyl chloride (12.3 g) in anhydrous toulene (150 ml) was added slowly with stirring to a solution of ethylamine (10 g) in dry ether (100 ml) at room temperature. The reaction mixture was heated at reflux for one hour, and the solvent and excess amine were then removed under reduced pressure. The residue was triturated with water, filtered, and recrystallized from ethanol-water to give trans 3-bromo-N-ethylcinnamamide, m.p. 89°-90° C., as a white crystalline material. NMR and IR spectra as well as elemental analysis were consistent with the assigned structure.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for one hour
  3. customthe solvent and excess amine were then removed under reduced pressure
  4. customThe residue was triturated with water
  5. filtrationfiltered
  6. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-417a24b2ff8c498d8e80c9bcf3a0ca44
Source dataset
uspto-grants-1978_05
Patent number
US04091112

Reaction notes

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