Potassium Iodide → HCID 23614537, compound

HRID 750970Notes

Reaction equation

HRID 750970 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[OH-].[Na+].[I-].[K+].Br[CH2:11][CH2:12][CH:13]=[CH2:14]>CC(O)(CC)C>[CH2:14]([N:2]1[N:3]=[CH:4][CH:5]=[N:1]1)[CH2:13][CH:12]=[CH2:11]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 21241Homoallyl bromideHCID 178418936HCID 178418936, compound

Product 1

HCID 23614537HCID 23614537, compoundYield 3.5%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent2×

Procedure

1H-[1,2,3]Triazole (10.36 g, 0.15 mol), sodium hydroxide (6 g, 0.15 mol) and potassium iodide (2.49 g, 0.015 mol) were dissolved in 2-methyl-2-butanol (50 ml) and heated to reflux for 1 h. At this temperature 4-bromo-but-1-ene (20.25 g, 0.15 mol) in 2-methyl-2-butanol (20 ml) were added dropwise and the resulting mixture was heated at reflux temperature for 4 h. After removal of the solvent the residue was taken up in ethyl acetate (100 ml), washed with water (3×50 ml), dried over sodium sulfate and concentrated. The crude product was purified by distillation yielding 0.65 g 2-but-3-enyl-2H-[1,2,3]triazole (b.p. 90-100° C. at 10 mbar),

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. temperaturethe resulting mixture was heated
  4. temperatureat reflux temperature for 4 h
  5. customAfter removal of the solvent the residue
  6. washwashed with water (3×50 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-dcf8a5976181460596feaa8ae254fcc1
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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