Hydroxyamine hydrochloride → 3-Methyl-5-(2-nitrophenyl)-1,2,4-oxadiazole

HRID 1816300Notes

Reaction equation

HRID 1816300 reaction equation
Cl.[NH2:2]O.CN([CH2:7][CH:8]=[N:9][C:10](=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18])C>[OH-].[Na+].O>[CH3:7][C:8]1[N:9]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])[O:20][N:2]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 57019786N-[(dimethylamino)ethylidene]-2-nitrobenzamide

Product 1

HCID 126766793-Methyl-5-(2-nitrophenyl)-1,2,4-oxadiazoleYield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of hydroxylamine hydrochloride (1.37 g, 20.1 mmol) in 5N aqueous sodium hydroxide (3.9 mL) was added N-[(dimethylamino)ethylidene]-2-nitrobenzamide (3.7 g, 15.7 mmol) portionwise. After stirring 20 minutes, the reaction was diluted with water (30 mL) and placed in a −23° C. freezer for 1 hour. The yellow crystals were collected by filtration. This material was dissolved in glacial acetic acid and heated to 110° C. for 14 hours. Toluene (30 mL) was added and the reaction fitted with a Dean-Stark Trap. The toluene was removed by distillation over a 2 hour period, and after cooling, water was added to the reaction mixture. After 2 hours in a −23° C. freezer, the precipitate was collected by filtration and rinsed with water to give 3-methyl-5-(2-nitrophenyl)-1,2,4-oxadiazole (2.63 g).

Workup

  1. waitplaced in a −23° C. freezer for 1 hour
  2. filtrationThe yellow crystals were collected by filtration
  3. dissolutionThis material was dissolved in glacial acetic acid
  4. additionToluene (30 mL) was added
  5. customthe reaction fitted with a Dean-Stark Trap
  6. customThe toluene was removed by distillation over a 2 hour period
  7. temperatureafter cooling
  8. additionwater was added to the reaction mixture
  9. waitAfter 2 hours in a −23° C. freezer
  10. filtrationthe precipitate was collected by filtration
  11. washrinsed with water

Sources & evidence

ORD record
ord-f4e026f59751454ba05e927614b84e5d
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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