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

HRID 517575Notes

Reaction equation

HRID 517575 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: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)=[C:2]2[CH2:3][C:4](=[O:6])[NH:5][C:1]2=[O:7])[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-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

Maleimide (0.60 g, 6.05 mmol) and triphenylphosphine (1.57 g, 5.97 mmol) were dissolved in 40 mL of acetone and the reaction mixture was stirred at 65° C. for 1 h. After cooling down to room temperature, the solid was collected by filtration, washed with acetone, and dried to afford compound 11 in 82.5% (1.77 g) yield as a white solid.

Workup

  1. temperatureAfter cooling down to room temperature
  2. filtrationthe solid was collected by filtration
  3. washwashed with acetone
  4. customdried

Sources & evidence

ORD record
ord-2d3d3a87e4474d68aacab52f9b4021f4
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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