Iodobenzene → 1-Phenyl-1H-1,2,3-triazole

HRID 1157341Notes

Reaction equation

HRID 1157341 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu](I)I>[C:7]1([N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 178418936HCID 178418936, compound

Product 1

HCID 2700091-Phenyl-1H-1,2,3-triazole

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

1,2,3-Triazole (5 g), iodobenzene (9.72 ml) and copper iodide (0.68 g) was taken in dry DMF under Nitrogen atmosphere. 1,2-(N,N-dimethyl) cyclohexyl diamine (1.02 g) and potassium phosphate (30.73 g) was added into above mixture. The reaction mixture was reflux at 110° C. for over night. TLC was checked no starting material and the reaction mixture was filtered through celite. The filtrate was diluted with water and product was extracted with dichloromethane. The organic layer was evaporated and the crude product was purified by column chromatography using 60-120 silica gel and pet ether \ ethyl acetate as eluent to give 1-phenyl-1H-1,2,3-triazole as white solid.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. additionThe filtrate was diluted with water and product
  3. extractionwas extracted with dichloromethane
  4. customThe organic layer was evaporated
  5. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-99f59dfbadbc42d9ad698a817962c7e0
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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