Aniline → N-Phenylphthalimide

HRID 2107341Notes

Reaction equation

HRID 2107341 reaction equation
[C]=[O:2].I[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1I.N[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[N:19]([CH3:23])[C:20](=[O:22])C>C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:4]1([N:19]2[C:20](=[O:22])[C:12]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:13]3[C:23]2=[O:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 119941,2-DiiodobenzeneHCID 31374DimethylacetamideHCID 178418416HCID 178418416, compound

Product 1

HCID 68215N-PhenylphthalimideYield 19%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6212ChloroformSolvent

Procedure

To a dry 3-neck, 25 mL round bottom flask equipped with a Teflon® resin coated stir bar, a balloon filled with carbon monoxide and a vacuum/argon inlet was placed o-diiodobenzene (320 mg, 0.97 mmol), aniline (90 mg, 0.97 mmol), palladium tetrakis(triphenylphosphine) (PdL4) (56 mg, 0.048 mmol=5%) and N,N-dimethylacetamide (DMAc, 2.9 mL). The mixture was stirred and degassed three times with argon, and then the argon atmosphere was replaced with carbon monoxide by three successive evacuations of the flask. The flask was then immersed in a 115° C. oil bath and heated until the reagents had dissolved. Then 1,8-diazobicyclo[5,4,0]undec-7-ene (DBU, 320 μl, 2.13 mmol) was added by syringe. After about 12 hours the product was produced in quantitative yield as determined by gas chromatography. The mixture was cooled, diluted with chloroform, extracted with water, dried over MgSO4, precipitated with methanol, collected by filtration, and dried in vacuo to give 40 mg product (19%). Much of the product remained in the filtrate.

Workup

  1. customdegassed three times with argon
  2. customwas then immersed in a 115° C.
  3. temperatureheated until the reagents
  4. dissolutionhad dissolved
  5. customAfter about 12 hours the product was produced in quantitative yield
  6. temperatureThe mixture was cooled
  7. extractionextracted with water
  8. dry with materialdried over MgSO4
  9. customprecipitated with methanol
  10. filtrationcollected by filtration
  11. customdried in vacuo

Sources & evidence

ORD record
ord-6358a8fc171e4546934fd49bea9567b2
Source dataset
uspto-grants-1990_06
Patent number
US04933467

Reaction notes

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