N,N,N',N'-Tetramethylethylenediamine → HCID 54381463, compound

HRID 1483816Notes

Reaction equation

HRID 1483816 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.CN(C)CCN(C)C.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>>[CH3:23][N:22]([CH3:24])[CH:21]=[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:9]#[N:10]

Participants

4

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 73722m-ChlorophenylacetonitrileHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 54381463HCID 54381463, compoundYield 100%

Procedure

A mixture of 3-chlorophenylacetonitrile (5 grams, 33.0 mmol), N,N,N′,N′-tetramethyl-ethane-1,2-diamine (0.767 grams, 6.60 mmol), and dimethyl formamide dimethyl acetal (20 mL) were heated at reflux for 4 h. On cooling, the reaction was partitioned between EtOAc and saturated aqueous NH4Cl solution. The aqueous phase was extracted with ethyl acetate and the combined organic phase washed with brine and concentrated in vacuo. The crude product was purified by chromatography (ethyl acetate/hexane, 0-10%) on silica gel (24 grams) to give pure product (6.8 grams, 33.0 mmol, 100% yield.).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 4 h
  3. temperatureOn cooling
  4. customthe reaction was partitioned between EtOAc and saturated aqueous NH4Cl solution
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic phase washed with brine
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography (ethyl acetate/hexane, 0-10%) on silica gel (24 grams)
  9. customto give pure product (6.8 grams, 33.0 mmol, 100% yield.)

Sources & evidence

ORD record
ord-6087f2dd2d4b4a23ae0db15293f91b7f
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

Loading…