Sodium Iodide → HCID 66692923, compound

HRID 1469186Notes

Reaction equation

HRID 1469186 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]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1.[Na+].[I-:17].CNCCNC>O1CCOCC1.[Cu]I>[I:17][C:2]1[S:6][C:5]([CH3:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 66693659HCID 66693659, compound

Product 1

HCID 66692923HCID 66692923, 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 12 (960 mg, 3.39 mmol) in 1.4-dioxane (10 mL) were added NaI (1.1 g, 6.78 mmol), CuI (100 mg, 0.34 mmol) and N1,N2-dimethylethane-1,2-diamine (0.1 mL, 0.68 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 23 was dried under high vacuum and used without further purification (540 mg, 48%).

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 23 was dried under high vacuum
  9. customused without further purification (540 mg, 48%)

Sources & evidence

ORD record
ord-14a63e104af74e12bc3b5a8754e3e906
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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