Sodium Iodide → HCID 12992843, compound

HRID 352060Notes

Reaction equation

HRID 352060 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[I-].[Na+].[OH-].[Na+].Cl[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>C(O)(CC)(C)C.C1(C)C=CC=CC=1>[C:12]1([CH2:11][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[C:12]1([CH2:11][N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 68451-ChloromethylnaphthaleneHCID 14798Sodium HydroxideHCID 178418936HCID 178418936, compound

Product 2

HCID 12992843HCID 12992843, compoundYield 84%HCID 12992844HCID 12992844, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 64052-Methyl-2-butanolSolvent2×

Procedure

1,2,3-Triazole (1454 mg, 21.05 mmol), sodium iodide (2103 mg, 14.03 mmol) and sodium hydroxide (842 mg, 21.05 mmol) were added to t-amyl alcohol (5.5 ml), and the mixture was refluxed under stirring for 1 hour. 1-(Chloromethyl)naphthalene (2478 mg, 14.03 mmol) was dissolved in t-amyl alcohol (5.5 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 ml×2), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1→1/3) to give 1-(1-naphthylmethyl)-1H-1,2,3-triazole (2.47 g) as white crystals (yield 84%), and 2-(1-naphthylmethyl)-2H-1,2,3-triazole as a colorless oil (136 mg, yield 5%). 1-(1-naphthylmethyl)-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 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=2/1→1/3)

Sources & evidence

ORD record
ord-b99190135e4043b595f275dda7dcc88f
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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