Hydrochloric Acid → N-(2-cyanoethyl)glycine

Temperature

10 °C

Glycine (5 g, 67 mmol) was suspended in water (10 cm3) and TMAH (25% in water, 24.3 g, 67 mmol) was added slowly, keeping the temperature at <30° C. with an ice-bath. The mixture was then cooled to 10° C. and acrylonitrile (3.89 g, 73 mmol) was added. The mixture was stirred overnight, and allowed to warm to room temperature slowly. The mixture was then neutralized with HCl (6M, 11.1 cm3), concentrated to 15 cm3 and diluted to 100 cm3 with EtOH. The solid precipitated was collected by filtration, dissolved in hot water (6 cm3) and reprecipitated with EtOH (13 cm3) to give 2-(2-cyanoethylamino)acetic acid (5.94 g, 69.6%) as a white solid, mp 192° C. (lit mp 190-191° C.).

1. customat <30° C.
2. temperatureto warm to room temperature slowly
3. concentrationconcentrated to 15 cm3
4. additiondiluted to 100 cm3 with EtOH
5. customThe solid precipitated
6. filtrationwas collected by filtration
7. dissolutiondissolved in hot water (6 cm3)
8. customreprecipitated with EtOH (13 cm3)

ORD record

ord-500b8796ff2148108f7581c21915219b

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08062429B2