Iodine → HCID 68429651, compound

HRID 2267168Notes

Reaction equation

HRID 2267168 reaction equation
[C:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([Si](C)(C)C)[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:19]I>O1CCCC1.F[B-](F)(F)F.[Ag+]>[I:19][C:10]1[N:9]=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]=1[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 807IodineHCID 68430050HCID 68430050, compound

Product 1

HCID 68429651HCID 68429651, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-Phenyl-5-propyl-4-trimethylsilanyl-1H-[1,2,3]-triazole (260 mg) prepared in the above 1) was dissolved in 5.0 ml of tetrahydrofuran, 389 mg of silver tetrafluoroborate and 507 mg of iodine were added thereto and the mixture was stirred at room temperature for one night. The reaction solution was filtered through Celite, a saturated aqueous solution of sodium thiosulfate was added to the filtrate and the solvent was evaporated in vacuo. Water was added to the residue, the mixture was extracted with ethyl acetate and the ethyl acetate layer washed with a saturated saline solution and dried over sodium sulfate. After the solvent was evaporated in vacuo, the residue was separated and purified by a silica gel column chromatography (hexane/ethyl acetate=2/1) to give 180 mg of the title compound as a white solid.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. additiona saturated aqueous solution of sodium thiosulfate was added to the filtrate
  3. customthe solvent was evaporated in vacuo
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washthe ethyl acetate layer washed with a saturated saline solution
  7. dry with materialdried over sodium sulfate
  8. customAfter the solvent was evaporated in vacuo
  9. customthe residue was separated
  10. custompurified by a silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-d2fa63805f654bc6a16b1828e91c9318
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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