Sodium Iodide → HCID 66939273, compound

HRID 1257464Notes

Reaction equation

HRID 1257464 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH2:14]O)[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.C(Cl)(=O)C(Cl)=O.C(=O)([O-])O.[Na+].[I-:29].[Na+]>O1CCCC1.CC(C)=O.O>[I:29][CH2:14][C:11]1[S:12][CH:13]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:4]=2)[N:10]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 2726773HCID 2726773, compound

Product 1

HCID 66939273HCID 66939273, compoundYield 31.2%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution (5 mL) of the compound (1.2 g, 4.6 mmol) obtained in Example 190b in tetrahydrofuran was added oxalyl chloride (0.68 mL, 9.3 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. To a solution (20 mL) of the residue in acetone was added sodium iodide (2.1 g, 14 mmol), and the mixture was stirred at 70° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=90/10) to give the title compound (530 mg, 31% in 2 steps) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. stirringthe mixture was stirred at 70° C. for 3 hr
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe obtained organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by column chromatography (hexane-hexane/ethyl acetate=90/10)

Sources & evidence

ORD record
ord-0415a84df4e94733b78dee4b81f60415
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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