Sodium Iodide → 1-(4-phenylbutyl)-1H-1,2,3-triazole

HRID 352056Notes

Reaction equation

HRID 352056 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[I-].[Na+].[OH-].[Na+].Cl[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(CC)(C)C.C1(C)C=CC=CC=1>[C:15]1([CH2:14][CH2:13][CH2:12][CH2:11][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 78543(4-Chlorobutyl)benzeneHCID 178418936HCID 178418936, compound

Product 1

HCID 129928411-(4-phenylbutyl)-1H-1,2,3-triazoleYield 81%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 64052-Methyl-2-butanolSolvent2×

Procedure

1,2,3-Triazole (1623 mg, 23.5 mmol), sodium iodide (2353 mg, 15.7 mmol) and sodium hydroxide (940 mg, 23.5 mmol) were added to t-amyl alcohol (6.2 ml), and the mixture was refluxed under stirring for 1 hour. 1-Chloro-4-phenylbutane (2648 mg, 15.7 mmol) was dissolved in t-amyl alcohol (6.2 ml) and added dropwise under reflux over 1 hour. The mixture was refluxed under stirring for 2 hours and cooled to room temperature, and toluene (50 ml) was added. The mixture was washed with water (50 ml×2), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→1/3) to give 1-(4-phenylbutyl)-1H-1,2,3-triazole (2.56 g) as colorless oil. yield 81%. 2-(4-Phenylbutyl)-2H-1,2,3-triazole (360 mg) was obtained as a colorless oil (yield 11%). 1-(4-phenylbutyl)-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 2 hours
  6. washThe mixture was washed with water (50 ml×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=4/1→1/3)

Sources & evidence

ORD record
ord-36f704495f954f6789e7426e59c986c7
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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