Maleimide → 3-(Triphenyl-lambda~5~-phosphanylidene)pyrrolidine-2,5-dione

HRID 1504582Notes

Reaction equation

HRID 1504582 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CC(C)=O>[C:21]1([P:14](=[C:2]2[CH2:3][C:4](=[O:6])[NH:5][C:1]2=[O:7])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 10935MaleimideHCID 11776Triphenylphosphine

Product 1

HCID 136113833-(Triphenyl-lambda~5~-phosphanylidene)pyrrolidine-2,5-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In an anhydrous acetone (60 mL), a solution including maleimide (6 g, 61.81 mmol) and triphenylphosphine (16.2 g, 61.76 mmol) was refluxed for 1 hour. After cooling, a precipitate was filtered, and a filter cake was washed with cold acetone (20 mL). Under reduced pressure, the washed filter cake was dried to obtain a white solid Compound 36a (20.428 g, 92%). The solid was used in following steps without further purification.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationa precipitate was filtered
  4. washa filter cake was washed with cold acetone (20 mL)
  5. filtrationUnder reduced pressure, the washed filter cake
  6. customwas dried

Sources & evidence

ORD record
ord-74eaca3d33484bf1acd1c1c71bce6e22
Source dataset
uspto-grants-2015_12
Patent number
US09216148B2

Reaction notes

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