Phthalimide → HCID 69673799, compound

HRID 2041868Notes

Reaction equation

HRID 2041868 reaction equation
O1[CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[CH2:24](N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[CH3:2][CH:3]([N:17]1[C:13](=[O:23])[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16]1=[O:18])[CH2:4][C:5]#[C:24][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11575Iodobenzene

Product 1

HCID 69673799HCID 69673799, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Under a nitrogen atmosphere, 24 ml of tetrahydrofuran, 2.11 g of iodobenzene, and 6.2 ml of triethylamine were added to 367 mg of dichlorobis(triphenylphosphine)palladium, 100 mg of copper iodide, and 2.20 g of the phthalimide compound obtained in the above described stage. The obtained mixture was stirred under reflux for 8 hours. After completion of the stirring, the reaction solution was cooled to a room temperature, and a solid was then filtrated. The filtrate was concentrated, and the residue was then purified by column chromatography (Wako Gel C-200; toluene:ethyl acetate=9:1), so as to obtain 1.82 g of a phthalimide compound.

Workup

  1. customobtained in the
  2. temperatureunder reflux for 8 hours
  3. filtrationa solid was then filtrated
  4. concentrationThe filtrate was concentrated
  5. customthe residue was then purified by column chromatography (Wako Gel C-200; toluene:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-c42bafc7300e499f9ddf40ee1dae314d
Source dataset
uspto-grants-2013_11
Patent number
US08586505B2

Reaction notes

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