Triethylamine → Ethyl 3-(dimethylamino)-2-(2,3,4-trifluorobenzoyl)prop-2-enoate

HRID 600878Notes

Reaction equation

HRID 600878 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[CH3:17][N:18]([CH3:26])[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C>O1CCCC1.CN(C)C=O>[CH3:17][N:18]([CH3:26])[CH:19]=[C:20]([C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([F:12])=[C:10]([F:11])[C:2]=1[F:1])[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 3029322,3,4-Trifluorobenzoic acid

Product 1

HCID 67271975Ethyl 3-(dimethylamino)-2-(2,3,4-trifluorobenzoyl)prop-2-enoateYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixed solution of 2,3,4-trifluorobenzoic acid (10.3 g, 58.5 mmol), thionyl chloride (6.4 ml, 87.8 mmol) and a catalytic amount of dimethylformamide was heated under reflux for 30 minutes. After letting the reaction solution cool, the reaction solution was concentrated under a reduced pressure, toluene (30 ml) was added to the residue, and concentration under a reduced pressure was performed again. The residue obtained was then dissolved in tetrahydrofuran (20 ml), and the resulting solution was added to a tetrahydrofuran (40 ml) solution of ethyl β-dimethylaminoacrylate (9.20 g, 64.3 mmol) and triethylamine (10.2 ml, 73.1 mmol) while stirring and cooling with ice. The reaction mixture was then stirred at room temperature for 1.5 hours and then heated under reflux for 16.5 hours. After letting the reaction solution cool, the precipitated solids were removed by filtration and the filtrate was concentrated under a reduced pressure. The residue was then applied to a silica gel chromatography, and 15.1 g (86%) of the title compound was obtained from an n-hexane:ethyl acetate=3:1 eluate.

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperaturecool
  3. concentrationthe reaction solution was concentrated under a reduced pressure, toluene (30 ml)
  4. additionwas added to the residue, and concentration under a reduced pressure
  5. customThe residue obtained
  6. temperaturecooling with ice
  7. stirringThe reaction mixture was then stirred at room temperature for 1.5 hours
  8. temperatureheated
  9. temperatureunder reflux for 16.5 hours
  10. temperaturecool
  11. customthe precipitated solids were removed by filtration
  12. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-3bc63ab400d142d295db3c5443d5693a
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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