Ethanamine, 2,2,2-trifluoro- → Ethyl (E)-3-[2-(2,2,2-trifluoroethylcarbamoyl)-5-trifluoromethylphenyl]acrylate

HRID 2061636Notes

Reaction equation

HRID 2061636 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[CH:7][C:8]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)=[O:5])[CH3:2].[F:21][C:22]([F:26])([F:25])[CH2:23][NH2:24].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[F:21][C:22]([F:26])([F:25])[CH2:23][NH:24][C:10]([C:9]1[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:8]=1/[CH:7]=[CH:6]/[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:12]

Participants

5

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 10868DicyclohexylcarbodiimideHCID 689435302-(2-Ethoxycarbonylvinyl)-4-trifluoromethylbenzoic acid

Product 1

HCID 57678952Ethyl (E)-3-[2-(2,2,2-trifluoroethylcarbamoyl)-5-trifluoromethylphenyl]acrylateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.3 g of 2-(2-ethoxycarbonylvinyl)-4-trifluoromethylbenzoic acid (4.5 mmol) and 453 mg of 2,2,2-trifluoroethylamine (4.5 mmol) were dissolved in 5 ml of DMF and 0.93 g of DCC was added. The mixture was stirred at RT for 4 h. The urea by-product was removed by filtration and then the solvent was removed under reduced pressure. The residue was recrystallized from DIP to obtain 1.6 g (96%) of white crystals.

Workup

  1. customThe urea by-product was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was recrystallized from DIP

Sources & evidence

ORD record
ord-cbde025a2afb43beb4412b3b3998d5fc
Source dataset
uspto-grants-2012_10
Patent number
US08283374B2

Reaction notes

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