Sodium Iodide → HCID 10071331, compound

HRID 129481Notes

Reaction equation

HRID 129481 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[C:10](=[O:24])[N:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:8]=2[N:7]=[CH:6]1.[I-:25].[Na+]>C(#N)C>[I:25][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[C:10](=[O:24])[N:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:8]=2[N:7]=[CH:6]1

Participants

4

Reactant 2

HCID 5238Sodium Iodide2×HCID 10382531HCID 10382531, compound

Product 1

HCID 10071331HCID 10071331, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 200 ml of acetonitrile were added 18 g (0.052 mol) of Compound 68 obtained in Example 68 and 12 g (0.078 mol) of sodium iodide, and the mixture was refluxed for 24 hours. In the course of refluxing, 7.8 g (0.052 mol) of sodium iodide was added to the mixture. After cooling, the solvent was evaporated under reduced pressure and water was added to the residue. Then, extraction was carried out with chloroform, and the organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain a crude product. Recrystallization from ethyl acetate-nhexane gave 16 g (yield 73%) of Compound 69.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperatureIn the course of refluxing
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure and water
  5. additionwas added to the residue
  6. extractionThen, extraction
  7. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated under reduced pressure
  11. customto obtain a crude product
  12. customRecrystallization from ethyl acetate-nhexane

Sources & evidence

ORD record
ord-cf17c07bd2ab47ca861d8e08f0194605
Source dataset
uspto-grants-1995_11
Patent number
US05468756

Reaction notes

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