Methylamine → trans 3-bromo-N-methylcinnamamide

HRID 441561Notes

Reaction equation

HRID 441561 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 1 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 1 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-003ef67a94ef40c7bce81b5c1eafdba4
Source dataset
uspto-grants-1977_08
Patent number
US04041071

Reaction notes

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