Sodium Iodide → N-[1-(4-iodophenyl)ethyl]acetamide

HRID 40559Notes

Reaction equation

HRID 40559 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=1.[Na+].[I-:15]>O1CCOCC1.[Cu]I>[I:15][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 2854373N-[1-(4-bromophenyl)ethyl]acetamide

Product 1

HCID 66634769N-[1-(4-iodophenyl)ethyl]acetamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To 8.70 g (35.9 mmol) N-(1-(4-bromophenyl)ethyl)acetamide (III.2) in 100 mL 1,4-dioxane are added 0.69 g (3.62 mmol) CuI, 0.97 mL (9.11 mmol) N,N″-dimethyl-ethylendiamine and 10.8 g (71.9 mmol) NaI. The reaction mixture is stirred at 120° C. for 3 d. The mixture is allowed to cool to r.t. and half of the solvent is removed in vacuo. EtOAc and diluted aq. ammonia solution are added and the layers are separated. The aq. layer is once more extracted with EtOAc. The organic layers are combined, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is triturated with diethylether and dried in vacuo.

Workup

  1. temperatureto cool to r.t.
  2. customhalf of the solvent is removed in vacuo
  3. additionEtOAc and diluted aq. ammonia solution are added
  4. customthe layers are separated
  5. extractionThe aq. layer is once more extracted with EtOAc
  6. dry with materialdried with Na2SO4
  7. customthe solvent is removed in vacuo
  8. customThe crude product is triturated with diethylether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-9522183961e34526b56b95da231a4cb1
Source dataset
uspto-grants-2013_09
Patent number
US08530460B2

Reaction notes

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