Carbon Tetrachloride → 1-(1-Chloroethyl)pyrrolidine-2,5-dione

N-vinylsuccinimide, 50.0 g. (0.40 mole) is dissolved in 1000 ml. carbon tetrachloride, 5.20 g. (0.020 mole) of stannic chloride is added and the mixture is stirred while saturating with hydrogen chloride for 6 hours at 20-30° C. After 24 hours, the mixture is resaturated with hydrogen chloride for 1.5 hours. At the end of 48 hours, the solution is decanted and the gummy residue is washed with ten 100 ml. portions of carbon tetrachloride. The combined extracts are slurried with 10 g. of diatomaceous earth, filtered an the filtrate concentrated under reduced pressure to approximately 400 ml. The N-(1-chloro-ethyl)-succinimide is filtered and dried at 20°-30° C. under reduced pressure to yield 38.4 g. (59%) of white solid melting at 83.5°-84.5° C.

1. dissolution(0.40 mole) is dissolved in 1000 ml
2. concentrationwhile saturating with hydrogen chloride for 6 hours at 20-30° C
3. waitthe mixture is resaturated with hydrogen chloride for 1.5 hours
4. customAt the end of 48 hours, the solution is decanted
5. washthe gummy residue is washed with ten 100 ml
6. filtrationof diatomaceous earth, filtered an the filtrate
7. concentrationconcentrated under reduced pressure to approximately 400 ml
8. filtrationThe N-(1-chloro-ethyl)-succinimide is filtered
9. customdried at 20°-30° C. under reduced pressure
10. customto yield 38.4 g

ORD record

ord-8b1d9cb1ce7341e1902728591f4e0ace

Source dataset

uspto-grants-1977_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04051169