Hydrochloric Acid → 3-(3-bromophenyl)-N-ethylprop-2-enamide

HRID 441560Notes

Reaction equation

HRID 441560 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)/[CH:5]=[CH:6]/[C:7]([O:9]CC)=O.[CH2:15]([NH2:17])[CH3:16].C[O-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH:5]=[CH:6][C:7]([NH:17][CH2:15][CH3:16])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 5369361Ethyl 3-(3-bromophenyl)acrylateHCID 10942334Sodium Methoxide

Product 1

HCID 427543-(3-bromophenyl)-N-ethylprop-2-enamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

Trans ethyl 3-bromocinnamate (8.4 g), ethylamine (6.7 g), methanol (18 ml) and 4A molecular sieves (1 g) were combined and heated at reflux for 1/2 hour. The mixture was cooled to about 45° C. and sodium methylate (0.6 g) added. The mixture was then heated at reflux 11/2 hour and then cooled. It was acidified with concentrated hydrochloric acid (12 ml). The sieves were removed by filtration. Ice water was added to the filtrate to precipitate trans 3-bromo-N-ethylcinnamamide, m.p. 89°-90° C. (after recrystallization from ethanol/water).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1/2 hour
  3. temperatureThe mixture was then heated
  4. temperatureat reflux 11/2 hour
  5. temperaturecooled
  6. customThe sieves were removed by filtration
  7. additionIce water was added to the filtrate
  8. customto precipitate
  9. customtrans 3-bromo-N-ethylcinnamamide, m.p. 89°-90° C. (after recrystallization from ethanol/water)

Sources & evidence

ORD record
ord-ce7df936a4914e7a9cceb8701663e7c0
Source dataset
uspto-grants-1977_08
Patent number
US04041071

Reaction notes

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