Sodium Iodide → HCID 10702735, compound

HRID 352058Notes

Reaction equation

HRID 352058 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[I-].[Na+].[OH-].[Na+].Cl[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>C(O)(CC)(C)C.C1(C)C=CC=CC=1>[C:14]1([C:12](=[O:13])[CH2:11][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 107572-ChloroacetophenoneHCID 14798Sodium HydroxideHCID 178418936HCID 178418936, compound

Product 1

HCID 10702735HCID 10702735, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 64052-Methyl-2-butanolSolvent2×

Procedure

1,2,3-Triazole (1689 mg, 24.45 mmol), sodium iodide (2443 mg, 16.3 mmol) and sodium hydroxide (978 mg, 24.45 mmol) were added to t-amyl alcohol (6.5 ml), and the mixture was refluxed under stirring for 1 hour. 2-Chloro-1-phenylethanone (2520 mg, 16.3 mmol) was dissolved in t-amyl alcohol (13 ml) and added dropwise over 1 hour. The mixture was refluxed under stirring for 1 hour. The mixture was cooled to room temperature, 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=3/2→1/4) to give 1-phenyl-2-(1H-1,2,3-triazol-1-yl)ethanone (1.38 g) as brown crystals (yield 45%). 1-Phenyl-2-(2H-1,2,3-triazol-2-yl)ethanone (550 mg) was obtained as yellow crystals (yield 18%). 1-phenyl-2-(1H-1,2,3-triazol-1-yl)ethanone

Workup

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

Sources & evidence

ORD record
ord-6f289981d4a54f3d96b1acaacb001200
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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