Hydrogen Peroxide → 1-Dipropylcarbamoyl-3-propylsulphinyl-1,2,4-triazole

HRID 371600Notes

Reaction equation

HRID 371600 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[C:5]([N:7]1[CH:11]=[N:10][C:9]([S:12][CH2:13][CH2:14][CH3:15])=[N:8]1)=[O:6])[CH2:2][CH3:3].[OH:19]O>C(O)(=O)C>[CH2:16]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([N:7]1[CH:11]=[N:10][C:9]([S:12]([CH2:13][CH2:14][CH3:15])=[O:19])=[N:8]1)=[O:6])[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 203549191-Dipropylcarbamoyl-3-propylthio-1,2,4-triazole

Product 1

HCID 203551191-Dipropylcarbamoyl-3-propylsulphinyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 13.5 g. 1-dipropylcarbamoyl-3-propylthio-1,2,4-triazole and 100 vol. hydrogen peroxide solution (5.7 ml., 1.0 molecular proportion) in 450 ml. glacial acetic acid was kept at room temperature for 14 days. The resulting solution was evaporated to dryness under reduced pressure and the residual oil was dissolved in methylene dichloride. The resulting solution was washed successively with 0.5N sodium hydroxide solution, and 0.5N hydrochloric acid. Solvent was removed from the solution by distillation under reduced pressure to give a residual oil which solidified on cooling. The solid product was recrystallized from benzene/petroleum ether, b.p. 40° - 60° C. to give 1-dipropylcarbamoyl-3-propylsulphinyl-1,2,4-triazole, m.p. 51° - 52.5° C. Elemental analysis satisfactory.

Workup

  1. customThe resulting solution was evaporated to dryness under reduced pressure
  2. dissolutionthe residual oil was dissolved in methylene dichloride
  3. washThe resulting solution was washed successively with 0.5N sodium hydroxide solution, and 0.5N hydrochloric acid
  4. customSolvent was removed from the solution by distillation under reduced pressure
  5. customto give a residual oil which
  6. temperatureon cooling
  7. customThe solid product was recrystallized from benzene/petroleum ether, b.p. 40° - 60° C.

Sources & evidence

ORD record
ord-c69623ee67e7461984a546ce945f9759
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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