Acrylonitrile → 65195-19-9

Temperature

80 °C

Compound 18 was prepared by modification of a reported procedure by Lynn (U.S. Pat. No. 2,975,187). To a vigorously stirred mixture of 2-oxazolidinone (87 g, 1 mol), 50% sodium hydroxide (w/w, 4 g) and toluene (250 mL) maintained at 55°-60° C., acrylonitrile (106 g, 2 mol) was added dropwise over a period of 30 min. The mixture was then stirred at 80° C. for 1 h and refluxed for 3 h. Additional acrylonitrile (50 mL) was added towards the end of the reaction to drive it to completion. Excess acrylonitrile was removed by distillation, and the residue was left at room temperature overnight. The mixture was filtered, cooled in an ice bath and acidified with concentrated H2SO4 to ~ pH 1. The salt was removed by filtration, and the filtrate was dried over anhydrous MgSO4. The residue obtained after removal of the solvent under vacuum was dried under high vacuum overnight to give 117 g (84%) of 18 as a colorless oil: 1H NMR (CDCl3) δ 2.68 (t, 2, CH2CH2CN), 3.57 (t, 2, NCH2CH 2), 3.75 (t, 2, NCH2CH2O) and 4.39 (t, 2, CH2H2O--).

1. customCompound 18 was prepared by modification of a reported procedure by Lynn (U.S
2. temperaturemaintained at 55°-60° C.
3. temperaturerefluxed for 3 h
4. customExcess acrylonitrile was removed by distillation
5. waitthe residue was left at room temperature overnight
6. filtrationThe mixture was filtered
7. temperaturecooled in an ice bath
8. customThe salt was removed by filtration
9. dry with materialthe filtrate was dried over anhydrous MgSO4
10. customThe residue obtained
11. customafter removal of the solvent under vacuum
12. customwas dried under high vacuum overnight

ORD record

ord-eec88b1b75b6403db1d011279c312570

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05298499