Potassium Iodide → HCID 10733908, compound

HRID 380970Notes

Reaction equation

HRID 380970 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 (SiO2, 20% EtOAc:Hexanes) to give 36.2 g (76%) of the pure product. NMR was consistent with the proposed title structure.

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 (SiO2, 20% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-40567260b37948a8bf1ee44d780745c2
Source dataset
uspto-grants-2001_10
Patent number
US06303816B1

Reaction notes

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