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

HRID 1833526Notes

Reaction equation

HRID 1833526 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, mp. 98°-101° C; νmax (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-da0c5ad5b1ca495282ea725af7fabb8d
Source dataset
uspto-grants-1978_01
Patent number
US04066752

Reaction notes

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