Triphenylphosphine → HCID 21201133, compound

HRID 1978801Notes

Reaction equation

HRID 1978801 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7]O)([O-:3])=[O:2].[C:15]1([C:21]2[C:22]([NH:24][C:25](=[O:27])[CH:26]=2)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.O.C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][N:24]2[C:25](=[O:27])[CH:26]=[C:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:22]2=[O:23])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 1169783,5-Dinitrobenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 125852973-Phenyl-1H-pyrrole-2,5-dione

Product 1

HCID 21201133HCID 21201133, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 500 ml three-necked flask equipped with a stirring means and a dropping funnel were placed 7.92 g of 3,5-dinitrobenzyl alcohol, 6.90 g of α-phenylmaleimide and 11.5 g of triphenylphosphine, and the mixture was dissolved in 200 ml of THF with stirring. To the solution was added dropwise 20.9 g of diethyl azodicarboxylate (as a 40% toluene solution) at 0° C. or lower. After the dropwise addition, the temperature was allowed to rise to room temperature and stirring was continued for 24 hours. The reaction solution was poured into water and extracted three times with ethyl acetate. The organic layer was washed three times with water and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration and the organic layer was concentrated under reduced pressure. The resulting pale yellow crystal was collected by filtration with n-heptane and recrystallized twice from ethyl acetate to afford 10.41 g of N-(3,5-dinitrophenyl)methyl-α-phenylmaleimide.

Workup

  1. customIn a 500 ml three-necked flask equipped with a stirring means and a dropping funnel
  2. additionAfter the dropwise addition
  3. customto rise to room temperature
  4. stirringstirring
  5. extractionextracted three times with ethyl acetate
  6. washThe organic layer was washed three times with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe drying agent was separated by filtration
  9. concentrationthe organic layer was concentrated under reduced pressure
  10. filtrationThe resulting pale yellow crystal was collected by filtration with n-heptane
  11. customrecrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-47c6aea17bde49fd860717a1aa1db74c
Source dataset
uspto-grants-2001_05
Patent number
US06238752B1

Reaction notes

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