Methylamine → trans 3-bromo-N-methylcinnamamide

HRID 372482Notes

Reaction equation

HRID 372482 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].[CH3:13][NH2:14]>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([NH:14][CH3:13])=[O:8]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 14959106trans 3-Bromocinnamoyl chloride

Product 1

HCID 20327748trans 3-bromo-N-methylcinnamamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of trans 3-bromocinnamoyl chloride (5 g) in dry benzene (100 ml) was added with stirring to an ethereal (200 ml) solution of methylamine (3 g). After the addition was complete, a slow stream of methylamine gas was bubbled through the reaction mixture at room temperature for one hour. Solvent and excess amine were removed under reduced pressure. The crude product was triturated with water, filtered, and recrystallized from ethanol-water to give trans 3-bromo-N-methylcinnamamide, m.p. 147°-147.5° C. NMR, IR, and elemental analysis were consistent with this structure.

Workup

  1. additionAfter the addition
  2. customa slow stream of methylamine gas was bubbled through the reaction mixture at room temperature for one hour
  3. customSolvent and excess amine were removed under reduced pressure
  4. customThe crude product was triturated with water
  5. filtrationfiltered
  6. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-ae489c040dda47288ee03333979fc070
Source dataset
uspto-grants-1978_05
Patent number
US04091112

Reaction notes

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