Carbon Dioxide → Cyanoacetic acid

HRID 616433Notes

Reaction equation

HRID 616433 reaction equation
[CH2:1]=O.[C:3]([CH2:5][C:6]([OH:8])=[O:7])#[N:4].C(=O)=O.[CH3:12][NH:13][CH3:14]>>[CH3:12][N:13]([CH2:1][C:5](=[CH2:6])[C:3]#[N:4])[CH3:14].[C:3]([CH2:5][C:6]([OH:8])=[O:7])#[N:4]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 674DimethylamineHCID 712FormaldehydeHCID 9740Cyanoacetic acid

Product 2

HCID 9740Cyanoacetic acidYield 31%HCID 32597102-DimethylaminomethylacrylonitrileYield 23%

Conditions

Temperature
15 °C

Procedure

Aqueous formaldehyde (162 ml, 37%) was added slowly to a solution of cyanacetic acid (85g) and dimethylamine (350 ml, 26% aqueous). The solution was stirred at 15° C during the addition and then at 40° C for a further 30 minutes. Carbon dioxide evolution commenced at 31° C, the rate of evolution increasing with rising temperature. The solution was extracted with ether (3 × 250 ml), after drying over anhydrous sodium sulphate, the solvent was evaporated at atmospheric pressure to give an oil. The infrared spectrum of the oil showed two nitrile peaks (2240cm-1 and 2220cm-1) indicating the pressure of two compounds. Distillation of the mixture gave 2-dimethylaminomethylacrylonitrile (25g, 23%, boiling point 43° C/1.0mm) and 1,3-bis(dimethylamino) propane-2-nitrile (43g, 31% boiling point 57° C/0.8mm).

Workup

  1. customcommenced at 31° C
  2. temperaturethe rate of evolution increasing
  3. extractionThe solution was extracted with ether (3 × 250 ml)
  4. dry with materialafter drying over anhydrous sodium sulphate
  5. customthe solvent was evaporated at atmospheric pressure
  6. customto give an oil
  7. distillationDistillation of the mixture

Sources & evidence

ORD record
ord-81e7c19c183d4d7586ae969ed44752cc
Source dataset
uspto-grants-1978_02
Patent number
US04074051

Reaction notes

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