Potassium Iodide → HCID 178509721, compound

HRID 1111168Notes

Reaction equation

HRID 1111168 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[NH:11]1[CH:15]=[N:14][C:13]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=2)=[N:12]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 178509721HCID 178509721, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 39.2 g of alpha-bromo-p-tolunitrile in 1 L of acetone are added sequentially 20.72 g of 1,2,4-triazole, 27.8 g of potassium carbonate and 1.7 g of potassium iodide. The reaction is stirred for 8 hours at 55° under argon, cooled to room temperature, filtered and evaporated. The residue is partitioned between methylene chloride and water. The organic phase is separated, washed with brine, dried over sodium sulfate and evaporated. The resulting crystalline crude product is chromatographed on 300 g of silica with toluene and ethyl acetate (1:1 to 0:1) to yield 4-[1-(1,2,4-triazolyl)methyl]benzonitrile (see example 9).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue is partitioned between methylene chloride and water
  4. customThe organic phase is separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe resulting crystalline crude product is chromatographed on 300 g of silica with toluene and ethyl acetate (1:1 to 0:1)

Sources & evidence

ORD record
ord-dbadef2ab02647d982d3e7b0c087ef2d
Source dataset
uspto-grants-1990_12
Patent number
US04978672

Reaction notes

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