Acrylonitrile → 4-Cyano-2-diaminomethylene-butyric acid ethyl ester

HRID 1171184Notes

Reaction equation

HRID 1171184 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:10])[CH:6]=[C:7]([NH2:9])[NH2:8])[CH3:3].C(N(CC)CC)C.[C:18](#[N:21])[CH:19]=[CH2:20]>O1CCCC1>[CH2:2]([O:4][C:5](=[O:10])[C:6]([CH2:20][CH2:19][C:18]#[N:21])=[C:7]([NH2:9])[NH2:8])[CH3:3]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 124946853,3-Diamino-acrylic acid ethyl ester hydrochloride

Product 1

HCID 124949064-Cyano-2-diaminomethylene-butyric acid ethyl esterYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The resulting 3,3-diamino-acrylic acid ethyl ester hydrochloride (2.2 g, 13.2 mmol) was suspended in tetrahydrofuran (40 mL) followed by the addition of triethylamine (2 mL, 14.3 mmol) and acrylonitrile (1.2 mL, 19.3 mmol) and refluxing while heating for 6 hours. Following completion of the reaction, the resulting triethylamine hydrochloride was filtered out and the filtrate was concentrated to obtain the title compound (0.6 g, 3.3 mmol, 25%).

Workup

  1. temperaturerefluxing
  2. temperaturewhile heating for 6 hours
  3. customcompletion of the reaction
  4. filtrationthe resulting triethylamine hydrochloride was filtered out
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2ca895c509b94913a9a403f59a44bd3b
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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