Potassium Iodide → HCID 178509660, compound

HRID 1746446Notes

Reaction equation

HRID 1746446 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[I-].[K+].BrC[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1>CC(C)=O.CO.C(O)(=O)C>[NH:19]1[CH:23]=[N:22][C:21]([CH2:1][C:13]2[CH:12]=[CH:11][CH:18]=[CH:17][C:14]=2[C:15]#[N:16])=[N:20]1

Participants

8

Reactant 4

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

Product 1

HCID 178509660HCID 178509660, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

Potassium carbonate (70 g, 0.507 mole) and potassium iodide (8.4 g, 0.051 mole) were added to a solution of 4-bromomethylbenzonitrile (100 g, 0.510 mole) in acetone (500 ml). To this reaction mixture, a solution of 1,2,4-triazole (35 g, 0.507 mole) in methanol (500 ml) was slowly added under nitrogen at 25 to 35° C. over a period of 1 hour. The reaction mixture was stirred for a further two to four hours and, after completion of the reaction, the solid was filtered and the filtrate was concentrated by distillation at 40 to 45° C. under reduced pressure. Water (2000 ml) was added to the residue and the pH of reaction mixture was adjusted to between 6 and 7 with acetic acid (3 to 4 ml). The aqueous layer was extracted with dichloromethane (2000 ml) and the organic extract was washed with water (200 ml) and the organic solvent was removed by distillation at 40 to 45° C. under reduced pressure to afford 4-[(1-(1,2,4-triazolyl)methyl]-benzonitrile (III) as a crude residue.

Workup

  1. customafter completion of the reaction
  2. filtrationthe solid was filtered
  3. concentrationthe filtrate was concentrated by distillation at 40 to 45° C. under reduced pressure
  4. additionWater (2000 ml) was added to the residue
  5. customthe pH of reaction mixture
  6. extractionThe aqueous layer was extracted with dichloromethane (2000 ml)
  7. extractionthe organic extract
  8. washwas washed with water (200 ml)
  9. customthe organic solvent was removed by distillation at 40 to 45° C. under reduced pressure

Sources & evidence

ORD record
ord-86b9c791ed6b4b60a682912efd35b1db
Source dataset
uspto-grants-2015_10
Patent number
US09150524B2

Reaction notes

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