Isopropylamine → 3-Bromo-N-isopropylcinnamamide

HRID 441557Notes

Reaction equation

HRID 441557 reaction equation
BrC1C=C(C=CC=1)/C=C/C(Cl)=O.C(N)(C)C.[Br:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][CH:31]=1)/[CH:21]=[CH:22]/[C:23]([NH:25][CH:26]([CH3:28])[CH3:27])=[O:24]>C1(C)C=CC=CC=1.CCOCC>[Br:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][CH:31]=1)[CH:21]=[CH:22][C:23]([NH:25][CH:26]([CH3:28])[CH3:27])=[O:24]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 14959106trans 3-Bromocinnamoyl chlorideHCID 20327747trans 3-bromo-N-isopropylcinnamamide

Product 1

HCID 543874693-Bromo-N-isopropylcinnamamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Trans m-bromocinnamic acid (11.4 g) in dry benzene (75 ml) was heated to reflux and then a mixture of thionyl chloride (12 g) in dry benzene (50 ml) was added at such a rate as to maintain constant reflux. The reaction mixture was heated at reflux for an additional 2 hr. after the addition of thionyl chloride. The solvent and excess thionyl chloride were then removed under reduced pressure to give trans 3-bromocinnamoyl chloride (ca. 12.3 g). A solution of the 3-bromocinnamoyl chloride in toluene (150 ml) was added dropwise with stirring to a solution of isopropylamine (10 g) in ether (200 ml). The reaction mixture was stirred at room temperature for 1 hour and then heated at reflux for 1 hour. The solvent and excess amine were removed under reduced pressure. The crude residue was triturated with water, filtered, and recrystallized from ethanol-water to give white, crystalline trans 3-bromo-N-isopropylcinnamamide, m.p. 85°-86° C. Elemental analysis, NMR and IR spectra all confirmed the identity of the product.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customThe solvent and excess amine were removed under reduced pressure
  4. customThe crude residue was triturated with water
  5. filtrationfiltered
  6. customrecrystallized from ethanol-water
  7. customto give white

Sources & evidence

ORD record
ord-8ec62574c38b4e70aadcdd791ab8e962
Source dataset
uspto-grants-1977_08
Patent number
US04041071

Reaction notes

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