Potassium Iodide → HCID 10733908, compound

HRID 720560Notes

Reaction equation

HRID 720560 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[I-].[K+]>CN(C=O)C.O>[CH2:17]([N:1]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1)[CH2:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 770004-Aminophenylacetonitrile

Product 1

HCID 10733908HCID 10733908, compoundYield 153.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-aminophenylacetonitrile (20 g, 151.3 mmol) in dry DMF (150 ml) was treated with potassium carbonate (50.1 g, 363.1 mmol), benzyl bromide (54.4 g, 318 mmol), and potassium iodide (5 g, 0.2 30.3 mmol). The reaction mixture was stirred at room temperature for 12 h. Water (100 ml) was added to the mixture and the organic was extracted with ether (3×200 ml). The combined organic fraction was washed with brine (200 ml), dried over sodium sulfate and concentrated. The crude product was further purified by flash chromatography (SiO21 20% EtOAc:Hexanes) to give 36.2 g (76%) of the pure product. NMR was consistent with the proposed title structure. Field Desorption Mass Spectrum:M+=312.

Workup

  1. extractionthe organic was extracted with ether (3×200 ml)
  2. washThe combined organic fraction was washed with brine (200 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was further purified by flash chromatography (SiO21 20% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-52c0441de71e47be845fe7be1e3de5a3
Source dataset
uspto-grants-2006_11
Patent number
US07135487B2

Reaction notes

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