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

HRID 2278682Notes

Reaction equation

HRID 2278682 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 with dichloromethane. The obtained 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 (abbreviated as HMptz) was obtained (pale yellow powder, yield: 18%). A scheme of the synthesis 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 be heated
  4. extractionan organic layer was extracted with dichloromethane
  5. washThe obtained 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

Sources & evidence

ORD record
ord-db795cc22d944609b2cb8ffdf561faaa
Source dataset
uspto-grants-2015_09
Patent number
US09133173B2

Reaction notes

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