Ammonia → 1,2-Cyclopentanedicarboximide

HRID 1183800Notes

Reaction equation

HRID 1183800 reaction equation
[CH:1]1([C:11]([O:13]CC)=O)[CH2:5][CH2:4][CH2:3][CH:2]1[C:6](OCC)=[O:7].[NH3:16]>>[C:6]1(=[O:7])[CH:2]2[CH2:3][CH2:4][CH2:5][CH:1]2[C:11](=[O:13])[NH:16]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 3021700Diethyl cyclopentane-1,2-dicarboxylate

Product 1

HCID 1107091,2-CyclopentanedicarboximideYield 96%

Conditions

Temperature
130 °C

Procedure

Load 1 kg of diethyl 1,2-cyclopentanedicarboxylate and 1.02 kg of 27% ammonia into an autoclave. The reaction mixture is heated in the autoclave at a temperature of 130° C. for a minimum of 4 hours. After cooling to 60° C. and depressurisation, evaporation of the solvent is carried out. The residue is then subjected to pyrolysis at 280° C. for 1 hour. The imide is purified by distillation in vacuo (4-12 mbars) at a temperature of 200° C. After isolation, the title product is obtained in a yield of 96%.

Workup

  1. temperatureAfter cooling to 60° C.
  2. customdepressurisation, evaporation of the solvent
  3. distillationThe imide is purified by distillation in vacuo (4-12 mbars) at a temperature of 200° C

Sources & evidence

ORD record
ord-4a96273e15254919994c22d722200980
Source dataset
uspto-grants-2014_03
Patent number
US08664408B2

Reaction notes

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