Sodium Iodide → HCID 68043811, compound

HRID 1469180Notes

Reaction equation

HRID 1469180 reaction equation
Br[C:2]1[S:6][C:5]([CH3:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:3]=1.[Na+].[I-:18].CNCCNC>O1CCOCC1.[Cu]I>[I:18][C:2]1[S:6][C:5]([CH3:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 66692858HCID 66692858, compound

Product 1

HCID 68043811HCID 68043811, compound

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 a solution of bromide 10 (1.5 g, 5.05 mmol) in 1.4-dioxane (10 mL) were added NaI (1.5 g, 10.1 mmol), CuI (0.1 g, 0.51 mmol) and N1,N2-dimethylethane-1,2-diamine (0.11 mL, 1.01 mmol) at room temperature. The reaction mixture was evacuated and backfilled with nitrogen. The mixture was stirred 120° C. for 18 hours. The mixture was cooled to room temperature and filtered off through celite. The filtrate was extracted with EtOAc/H2O (50 mL/50 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product 11 was dried under high vacuum and used without further purification (2.32 g, 79%).

Workup

  1. customThe reaction mixture was evacuated
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered off through celite
  4. extractionThe filtrate was extracted with EtOAc/H2O (50 mL/50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dry with materialThe crude product 11 was dried under high vacuum
  9. customused without further purification (2.32 g, 79%)

Sources & evidence

ORD record
ord-b2e7b936f9194d35a31d49b3357fa683
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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