Carbon Dioxide → Cyanoacetic acid

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence