Ethyl cyanoacetate → Ethyl 2,3-Dicyanopropionate

HRID 2109003Notes

Reaction equation

HRID 2109003 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[C:9](#[N:12])[CH2:10]O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:1]([CH:3]([CH2:10][C:9]#[N:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

6

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 7857HydroxyacetonitrileHCID 11430Potassium Carbonate

Product 1

HCID 10725530Ethyl 2,3-Dicyanopropionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl cyanoacetate (916.0 g, 8.10 mol) in N,N-dimethylformamide (2.5 L) was added slowly glycolonitrile (700.0 g, 6.75 mol) in water (55% solution). To the mixture was added potassium carbonate (932.7 g, 6.75 mol), over 1.5 h, ensuring that the reaction temperature did not rise above 30° C. The reaction mixture was then stirred at room temperature overnight. The reaction mixture was filtered and the filtrate adjusted to pH 3 by addition of acid. The organic phase was separated and partially concentrated in vacuo. To the concentrate was added diethyl ether (1L) and the solution was washed with water (5×1 L), dried (MgSO4) and concentrated in vacuo to give Preparation 46 (803 g).

Workup

  1. customdid not rise above 30° C
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate adjusted to pH 3 by addition of acid
  4. customThe organic phase was separated
  5. concentrationpartially concentrated in vacuo
  6. additionTo the concentrate was added diethyl ether (1L)
  7. washthe solution was washed with water (5×1 L)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customto give

Sources & evidence

ORD record
ord-d53efb0fe59f4853998e6783b6775b96
Source dataset
uspto-grants-2009_04
Patent number
US07514464B2

Reaction notes

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