Methacrylic Acid → N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylprop-2-enamide

HRID 415960Notes

Reaction equation

HRID 415960 reaction equation
[CH3:1][C:2](=[CH2:6])[C:3](O)=[O:4].S(Cl)(Cl)=O.[C:11]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=1[C:20]([F:23])([F:22])[F:21])#[N:12]>CC(N(C)C)=O>[CH3:1][C:2](=[CH2:6])[C:3]([NH:17][C:16]1[CH:18]=[CH:19][C:13]([C:11]#[N:12])=[C:14]([C:20]([F:21])([F:22])[F:23])[CH:15]=1)=[O:4]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 24386Thionyl ChlorideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

Product 1

HCID 11149469N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylprop-2-enamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Methyl acrylic acid (510 mg, 6 mmol) in DMA (10 ml) was treated with thionyl chloride (714 mg, 6 mmol) at 0° C. The mixture was stirred for 30 min then 4-cyano-3-trifluoromethyl-aniline (1.0 g, 6.0 mmol) was added. The resulting suspension was stirred overnight and then quenched with NaHCO3. The reaction mixture was extracted with ethyl acetate, washed with brine and dried with Na2SO4. The resulting concentrated crude product was purified on column (Ethyl acetate:Hexane, 1:2) to yield the title compound as a yellow solid.

Workup

  1. stirringThe resulting suspension was stirred overnight
  2. customquenched with NaHCO3
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationThe resulting concentrated crude product
  7. customwas purified on column (Ethyl acetate:Hexane, 1:2)

Sources & evidence

ORD record
ord-64ae87baa426447298fd92b9bfa5606e
Source dataset
uspto-grants-2012_01
Patent number
US08088811B2

Reaction notes

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