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

HRID 1189594Notes

Reaction equation

HRID 1189594 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-bottom 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 perform heating. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried over magnesium sulfate. After the drying, the solution was filtered. 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 obtained (pale yellow powder, 18% yield). The synthesis scheme of Step 1 is shown below.

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 perform heating
  4. extractionan organic layer was extracted with dichloromethane
  5. washThe obtained organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter the drying, the solution was filtered
  8. distillationThe solvent of this solution was distilled off
  9. customthe resulting residue was purified by silica gel column chromatography which

Sources & evidence

ORD record
ord-f1118da01f5047d789521927895fdb13
Source dataset
uspto-grants-2014_03
Patent number
US08674114B2

Reaction notes

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