Acrylonitrile → N-(2-Cyanoethyl)glycine ethyl ester

139.6 g (1 mole) of glycine ethyl ester hydrochloride was dissolved in 80 ml of distilled water and to this solution was added 230 ml of an aqueous solution of 67.3 g (1.2 mole eq.) of potassium hydroxide. Then, 106.2 g (2 mole eq.) of acrylonitrile was added to the reaction solution while heating and stirring at 50° to 60° C. The reaction mixture was stirred for 5 hours with heating and then the organic layer was separated. The aqueous layer was extracted with ethyl ether and the extract was combined with the organic layer as separated above. The combined organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to remove the solvent. The residue was distilled under reduced pressure (100° to 150° C./10.25 torr) to obtain 65.6 g (Yield: 48%) of the title compound.

1. temperaturewhile heating
2. stirringThe reaction mixture was stirred for 5 hours
3. temperaturewith heating
4. customthe organic layer was separated
5. extractionThe aqueous layer was extracted with ethyl ether
6. customas separated above
7. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure
10. customto remove the solvent
11. distillationThe residue was distilled under reduced pressure (100° to 150° C./10.25 torr)

ORD record

ord-f0848681cbc9454dad55b7706f5d5ca1

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05869670