N,N,N',N'-Tetramethylethylenediamine → HCID 3790410, compound

HRID 1483811Notes

Reaction equation

HRID 1483811 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].CN(C)CCN(C)C>>[CH3:18][N:17]([CH3:19])[CH:16]=[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:12])[F:13])[CH:4]=1)[C:10]#[N:11]

Participants

4

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 75360m-TrifluoromethylphenylacetonitrileHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 3790410HCID 3790410, compoundYield 50%

Procedure

A mixture of 2-(3-(trifluoromethyl)phenyl)acetonitrile (4.55 g, 24.58 mmol), 1,1-dimethoxy-N,N-dimethylmethanamine (13.10 ml, 98 mmol), and N1,N1,N2,N2-tetramethylethane-1,2-diamine (0.737 ml, 4.92 mmol) were heated to reflux for 5 h. After cooling to RT, the mixture was partitioned between saturated aqueous NH4Cl and EtOAc and extracted three times with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo. After absorbing on celite, the compound was purified by Isco (40 g silica, 10% to 70% EtOAc/hexanes) to give pure 3-(dimethylamino)-2-(3-(trifluoromethyl)phenyl)acrylonitrile (2.93 g, 50% yield).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 5 h
  3. customthe mixture was partitioned between saturated aqueous NH4Cl and EtOAc
  4. extractionextracted three times with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customAfter absorbing on celite
  9. customthe compound was purified by Isco (40 g silica, 10% to 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-224aa9039bc841dc9eeb045c71b20295
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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