Sodium Iodide → 2-Benzyl-1,2,3-triazole

HRID 352059Notes

Reaction equation

HRID 352059 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[I-].[Na+].[OH-].[Na+].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(CC)(C)C.C1(C)C=CC=CC=1>[CH2:10]([N:1]1[CH:5]=[CH:4][N:3]=[N:2]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:10]([N:2]1[N:3]=[CH:4][CH:5]=[N:1]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 178418936HCID 178418936, compound

Product 2

HCID 1382031-Benzyl-1,2,3-triazoleHCID 53254672-Benzyl-1,2,3-triazoleYield 6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 64052-Methyl-2-butanolSolvent2×

Procedure

1,2,3-Triazole (1523 mg, 22.05 mmol), sodium iodide (2203 mg, 14.7 mmol) and sodium hydroxide (882 mg, 22.05 mmol) were added to t-amyl alcohol (5.8 ml), and the mixture was refluxed under stirring for 1 hour. Benzyl chloride (1861 mg, 14.7 mmol) was dissolved in t-amyl alcohol (5.8 ml) and added dropwise under reflux over 1 hour. The mixture was refluxed under stirring for 1 hour. The mixture was cooled to room temperature and toluene (50 ml) was added. The mixture was washed with water (50×2), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/3) to give 1-benzyl-1H-1,2,3-triazole (2.10 g) as white crystals, yield 90%, and 2-benzyl-2H-1,2,3-triazole (140 mg) as white crystals (yield 6%). 1-benzyl-1H-1,2,3-triazole

Workup

  1. temperaturethe mixture was refluxed
  2. additionadded dropwise
  3. temperatureunder reflux over 1 hour
  4. temperatureThe mixture was refluxed
  5. stirringunder stirring for 1 hour
  6. washThe mixture was washed with water (50×2)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/3)

Sources & evidence

ORD record
ord-0ce0019280cb4a238e5e3f72338e79a9
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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