1H-1,2,4-Triazole → HCID 86762316, compound

HRID 2364595Notes

Reaction equation

HRID 2364595 reaction equation
I[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[NH:10]1[CH:14]=[N:13][CH:12]=[N:11]1.CNC1CCCCC1NC.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cu]I>[CH3:9][C:4]1[CH:3]=[C:2]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamine

Product 1

HCID 86762316HCID 86762316, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-iodo-3,5-dimethylbenzene (6.25 mL, 43.1 mmol), 1H-1,2,4-triazole (5.95 g, 86 mmol), CuI (0.410 g, 2.155 mmol), N1,N2-dimethylcyclohexane-1,2-diamine (0.681 mL, 4.31 mmol) and K2CO3 (21.04 g, 99 mmol) in DMF (200 mL) was heated at 140° C. overnight. After cooling to room temperature, it was filtered through a short plug of Celite®. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with DCM/EtOAc (4/1) (v/v) as eluent to yield 1-(3,5-dimethylphenyl)-1H-1,2,4-triazole (6 g, 80%) as a liquid.

Workup

  1. filtrationit was filtered through a short plug of Celite®
  2. customUpon evaporation of the solvent
  3. customthe residue was purified by column chromatography on silica gel with DCM/EtOAc (4/1) (v/v) as eluent

Sources & evidence

ORD record
ord-03993b25bab5412bba72b0e16e47f7fb
Source dataset
uspto-grants-2014_04
Patent number
US08692241B1

Reaction notes

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