Potassium Carbonate → 4-methyl-3-(4-penten-1-yl)-5-phenyl-4H-1,2,4-triazole

HRID 550530Notes

Reaction equation

HRID 550530 reaction equation
Cl.[CH3:2][NH:3][C:4](=NC)[CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].C([O-])([O-])=O.[K+].[K+].[C:18]([NH:26][NH2:27])(=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[CH3:2][N:3]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:26][N:27]=[C:4]1[CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11955BenzoylhydrazineHCID 86630240N,N'-dimethyl-5-hexenimidamide hydrochloride

Product 1

HCID 576918864-methyl-3-(4-penten-1-yl)-5-phenyl-4H-1,2,4-triazoleYield 0%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N,N′-dimethyl-5-hexenimidamide hydrochloride (3.1Mmol) in MeOH (20 ml) were added K2CO3 (3.1Mmol) and benzhydrazide (3.1Mmol). The solution was heated to reflux for 24 h. Volatiles were evaporated in vacuo, the crude dissolved in DCM, washed with water and dried over Na2SO4. After filtration and concentration to dryness in vacuo, the crude was purified by column chromatography (DCM:MeOH=98 to 2) to give 196 mg of the title compound.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 24 h
  3. customVolatiles were evaporated in vacuo
  4. dissolutionthe crude dissolved in DCM
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration to dryness in vacuo
  8. customthe crude was purified by column chromatography (DCM:MeOH=98 to 2)

Sources & evidence

ORD record
ord-872fc588945d4b25b5d6cca8b78bfcdb
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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