1-Butanol → 3-Methyl-4,5-diphenyl-4H-1,2,4-triazole

HRID 2176331Notes

Reaction equation

HRID 2176331 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=S)[CH3:2].[C:11]([NH:19][NH2:20])(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)CCC>O>[CH3:2][C:1]1[N:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:19][N:20]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 11955BenzoylhydrazineHCID 820777N-Phenylethanethioamide

Product 1

HCID 122169033-Methyl-4,5-diphenyl-4H-1,2,4-triazoleYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 5.04 g of thioacetanilide, 5.44 g of benzoylhydrazine, and 50 mL of 1-butanol were put in a round-bottomed flask provided with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to be heated. Then, water was added to this solution and an organic layer was extracted from dichloromethane. The organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtrated. The solvent of this solution was distilled off, and the resulting residue was purified by silica gel column chromatography which uses ethyl acetate as a developing solvent, so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviation: HMptz) was prepared (light yellow powder, yield: 18%). The synthetic scheme of Step 1 is shown by (a-1).

Workup

  1. customprovided with a reflux pipe
  2. customThis reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes
  3. temperatureto be heated
  4. extractionan organic layer was extracted from dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationAfter the drying, the solution was filtrated
  8. distillationThe solvent of this solution was distilled off
  9. customthe resulting residue was purified by silica gel column chromatography which
  10. customso that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviation: HMptz) was prepared (light yellow powder, yield: 18%)

Sources & evidence

ORD record
ord-eb930c9a3bde4222b620f1f2eaf98f41
Source dataset
uspto-grants-2015_06
Patent number
US09065061B2

Reaction notes

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