Triethylamine → HCID 53640509, compound

HRID 525963Notes

Reaction equation

HRID 525963 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:17])[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[F:18][C:19]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:20]=1[C:21](Cl)=[O:22]>C1(C)C=CC=CC=1>[CH3:8][N:9]([CH3:17])[CH:10]=[C:11]([C:21](=[O:22])[C:20]1[CH:24]=[C:25]([F:29])[C:26]([F:28])=[CH:27][C:19]=1[F:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 1451642,4,5-Trifluorobenzoyl chloride

Product 1

HCID 53640509HCID 53640509, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of triethylamine (107 mL, 771 mmol) and ethyl 3-(dimethylamino)acrylate (55.2 mL, 386 mmol) in toluene (250 mL) was added dropwise a toluene solution of 2,4,5-trifluorobenzoyl chloride (50 g, 257 mmol). The mixture was stirred at 90° C. for 3 h. LCMS showed completion of reaction. After cooling down, the reaction mixture was washed with water and extracted with EA. The organic layer was dried over Na2SO4, filtered and concentrated to afford ethyl 3-(dimethylamino)-2-(2,4,5-trifluorobenzoyl)acrylate (65 g, 216 mmol, 84% yield) as a brown oil. LCMS: (M+H)+: 302.1.

Workup

  1. customcompletion of reaction
  2. temperatureAfter cooling down
  3. washthe reaction mixture was washed with water
  4. extractionextracted with EA
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-277f1a04a18a47f4a738b7db5e372231
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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