Sodium Iodide → HCID 178517845, compound

HRID 2106804Notes

Reaction equation

HRID 2106804 reaction equation
[I-].[Na+].Cl[Si](C)(C)C.[F:8][C:9]1[C:10]([O:22]C)=[N:11][CH:12]=[C:13]([O:15][C:16]([F:21])([F:20])[CH:17]([F:19])[F:18])[CH:14]=1>C(#N)C.C(Cl)Cl>[F:8][C:9]1[C:10]([OH:22])=[N:11][CH:12]=[C:13]([O:15][C:16]([F:20])([F:21])[CH:17]([F:18])[F:19])[CH:14]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 14837013HCID 14837013, compound

Product 1

HCID 178517845HCID 178517845, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium iodide (1.80 g, 12.0 mmol) and then chlorotrimethylsilane (1.5 ml, 11.8 mmol) were added to a solution of 3-fluoro-2-methoxy-5-(1,1,2,2-tetrafluoroethoxy)pyridine (1.65 g, 6.79 mmol) in 8 ml of acetonitrile with stirring and under nitrogen and the mixture was heated at reflux for 2 5 hours. It was then allowed to cool and was diluted with 20 ml of methylene chloride. The resulting solution was extracted with water and with saturated aqueous sodium hydroxide, dried over sodium sulfate, and concentrated by evaporation under reduced pressure to obtain the title compound as a solid. This was recrystallized from toluene to obtain 0.95 g of the product as a white solid. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 5 hours
  3. temperatureto cool
  4. extractionThe resulting solution was extracted with water and with saturated aqueous sodium hydroxide
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-81b3ec38246f49359ea141f79d32f6aa
Source dataset
uspto-grants-1990_06
Patent number
US04931452

Reaction notes

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