Ethyl Acetate → 1-{[(2,2,2-Trichloroethoxy)carbonyl]oxy}pyrrolidine-2,5-dione

HRID 894103Notes

Reaction equation

HRID 894103 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].C(OCC)(=O)C.[Cl:15][C:16]([Cl:23])([Cl:22])[CH2:17][O:18][C:19](Cl)=[O:20]>N1C=CC=CC=1>[Cl:15][C:16]([Cl:23])([Cl:22])[CH2:17][O:18][C:19]([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])=[O:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 80170N-HydroxysuccinimideHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 41921781-{[(2,2,2-Trichloroethoxy)carbonyl]oxy}pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve 5.75 gm. of N-hydroxysuccinimide in 200 ml. ethyl acetate and 4 gm. of pyridine; cool the resultant solution to 0° C. To this solution, add 10.6 gm. 2,2,2-trichloroethylchloroformate dropwise over a period of 1.5 hours. Filter the resultant mixture and evaporate the filtrate to dryness. Wash the thereby formed needles with hexane to obtain N-(2,2,2-trichloroethoxycarbonyloxy) succinimide, m.p. 98°-101° C.; ν max. (CHCl3) 1825, 1790, 1750, 1185, 826 cm.-1, δ (CDCl3) 2.85 (4H, s, --CO(CH2)2CO--) and 4.90 ppm (2H, s, --COOCH2CCl3).

Workup

  1. dissolutionDissolve 5.75 gm
  2. additionTo this solution, add 10.6 gm
  3. filtrationFilter the resultant mixture
  4. customevaporate the filtrate to dryness
  5. washWash the
  6. customthereby formed needles with hexane

Sources & evidence

ORD record
ord-990af25831704a208e34b777c0c39f2e
Source dataset
uspto-grants-1981_08
Patent number
US04282350

Reaction notes

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