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

HRID 574038Notes

Reaction equation

HRID 574038 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 into a round-bottom flask provided with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100W) for 2 hours and 45 minutes to be heated. Then, water was added to this solution and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried over magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled off, and the resulting residue was purified by silica gel column chromatography using ethyl acetate as a developing solvent, so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviation: HMptz) was obtained (a pale yellow powder, 18% yield). A scheme of the synthesis of Step 1 is shown in the following (c-1).

Workup

  1. customprovided with a reflux pipe
  2. temperatureto be heated
  3. extractionthe organic layer was extracted with dichloromethane
  4. washThe obtained organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe solution which had been dried
  7. filtrationwas filtered
  8. distillationThe solvent of this solution was distilled off
  9. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-127ecea26703432090bba95d1078c68e
Source dataset
uspto-grants-2015_05
Patent number
US09034486B2

Reaction notes

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