Acetonitrile → HCID 69671093, compound

HRID 529876Notes

Reaction equation

HRID 529876 reaction equation
Cl[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[CH:3][C:4]#[N:5].Cl.[CH2:14]([CH:16]1[CH2:18][CH:17]1[NH2:19])C.[CH3:20]C#N>>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:2]([NH:19][CH:17]([CH:16]([CH3:14])[CH3:18])[CH3:20])=[CH:3][C:4]#[N:5]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 129536982-Ethylcyclopropan-1-amine hydrochlorideHCID 713346313-Chloro-3-(2-chlorophenyl)prop-2-enenitrile

Product 1

HCID 69671093HCID 69671093, compoundYield 89%

Procedure

To a solution of 3-chloro-3-(2-chlorophenyl)acrylonitrile (1.2 g, 6.05 mmol, 1 eq.) in 15 ml of MeCN was added 2-ethylcyclopropanamine hydrochloride (0.633 g, 7.27 mmol, 1.2 eq.) followed by TEA (0.919 g, 7.08 mmol, 1.5 eq.). The reaction was microwaved (130° C., 2000 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was triturated in ethyl acetate and the white solid removed by filtration. After concentration under vacuum, the residual oil was subjected to column chromatography to give 3-(2-chlorophenyl)-3-[(3-methylbutan-2-yl)amino]acrylonitrile (1.36 g, 89% yield).

Workup

  1. customThe reaction was microwaved
  2. custom(130° C., 2000 s, fixed hold, high absorption)
  3. customthe solvent evaporated
  4. customThe residual oil was triturated in ethyl acetate
  5. customthe white solid removed by filtration
  6. concentrationAfter concentration under vacuum

Sources & evidence

ORD record
ord-b66505aed2234931a4c81b0e636f7142
Source dataset
uspto-grants-2016_05
Patent number
US09351489B2

Reaction notes

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