Hydrogen Peroxide → 3-(3-Ethoxy-4-nitrophenyl)-4-methyl-4H-1,2,4-triazole

HRID 523095Notes

Reaction equation

HRID 523095 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[N:14]([CH3:19])[C:15](S)=[N:16][N:17]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2].ClCCl.OO.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[N:14]([CH3:19])[CH:15]=[N:16][N:17]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 178466049HCID 178466049, compound

Product 1

HCID 899956773-(3-Ethoxy-4-nitrophenyl)-4-methyl-4H-1,2,4-triazoleYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-(3-Ethoxy-4-nitrophenyl)-4-methyl-4H-1,2,4-triazole-3-thiol (Preparation 117, 1.16 g 4.14 mmole) was stirred with dichloromethane (11.8 mL) and the suspension cooled in ice. A solution of 35% hydrogen peroxide (0.91 mL, 12.2 mmole) in acetic acid (6 mL) was added dropwise and the reaction was stirred at room temperature for 70 minutes. Dichloromethane (50 mL) was added followed by 2M aqueous sodium hydroxide (48 mL) to pH=7. The layers were separated, the aqueous extracted with more dichloromethane, the organic layers combined, dried over sodium sulphate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 5-10% EtOH in DCM to afford the title compound (607 mg, 60%).

Workup

  1. temperaturethe suspension cooled in ice
  2. customThe layers were separated
  3. extractionthe aqueous extracted with more dichloromethane
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 5-10% EtOH in DCM

Sources & evidence

ORD record
ord-5ba80a8cfd244973af37c5484d1d7a2c
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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