Sodium Iodide → N-(1-(4-Iodophenyl)propan-2-YL)acetamide

HRID 76162Notes

Reaction equation

HRID 76162 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12](=[O:14])[CH3:13])[CH3:10])=[CH:4][CH:3]=1.CNCCNC.[Na+].[I-:22]>O1CCOCC1.[Cu]I>[I:22][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12](=[O:14])[CH3:13])[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 45824256N-(1-(4-bromophenyl)propan-2-yl)acetamide

Product 1

HCID 66611344N-(1-(4-Iodophenyl)propan-2-YL)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 6.00 g (23.4 mmol) N-(1-(4-bromophenyl)propan-2-yl)acetamide (I44.1) in 65 mL dioxan are added 0.45 g (2.34 mmol) CuI, 0.50 mL (4.70 mmol) N,N′-dimethylethylendiamine and 7.02 g (46.9 mmol) NaI. The reaction mixture is stirred at 120° C. for 70 h. 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 at 50° C. 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 at 50° C. in vacuo

Sources & evidence

ORD record
ord-0f307e46944d4233a87b6d58561972ae
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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