Water → HCID 68672656, compound

HRID 1927664Notes

Reaction equation

HRID 1927664 reaction equation
[N+]([O-])([N+]([O-])=O)=O.N[C:8]1[CH:9]=[CH:10][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:12]([CH:15]=1)[C:13]#[N:14].[I-:22].[Na+].O>C(#N)C>[I:22][C:8]1[CH:9]=[CH:10][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:12]([CH:15]=1)[C:13]#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 25352Nitrogen oxide (N2O4)HCID 68673467HCID 68673467, compound

Product 1

HCID 68672656HCID 68672656, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dinitrogen tetroxide (2.2 equiv.) was added to a suspension of 5-amino-2-pyridin-2-ylbenzonitrile (0.85 mmol) in acetonitrile (8.5 mL) at −30° C. After 5 min, sodium iodide (1.28 mmol, 1.5 equiv.), and the mixture was stirred for 10 minutes. Water (10 mL) was added and the reaction was allowed to warm to room temperature over 30 min. The product was extracted with methylene chloride and the extracts were washed with saturated sodium thiosulfate solution and brine, dried over sodium sulfate and concentrated. The resulting residue was passed through a silica gel plug, rinsing with 2% methanol in methylene chloride to provide 5-iodo-2-pyridin-2-ylbenzonitrile, which was used without further purification.

Workup

  1. extractionThe product was extracted with methylene chloride
  2. washthe extracts were washed with saturated sodium thiosulfate solution and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. washrinsing with 2% methanol in methylene chloride

Sources & evidence

ORD record
ord-58d0412b36f042e395f760cfe6b7c88b
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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