Sodium sulfide nonahydrate → 2-(3-Methyl-1,2,4-oxadiazol-5-yl)aniline

HRID 1816301Notes

Reaction equation

HRID 1816301 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-])=O)[O:4][N:3]=1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>O1CCOCC1.O>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:13])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 73972Sodium sulfide nonahydrateHCID 126766793-Methyl-5-(2-nitrophenyl)-1,2,4-oxadiazole

Product 1

HCID 126766822-(3-Methyl-1,2,4-oxadiazol-5-yl)anilineYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-methyl-5-(2-nitrophenyl)-1,2,4-oxadiazole (1.0 g, 4.8 mmol) in dioxane (11 mL) at 80°0 C. was treated with 11 mL of an aqueous solution of sodium sulfide nonahydrate (2.55 g, 10.6 mmol), also at 80° C. After stirring at that temperature for 45 minutes, the reaction was diluted with water (15 mL) and cooled in an ice bath. The resulting precipitate was collected by filtration and rinsed with water to afford 3-methyl-5-(2-aminophenyl)-1,2,4-oxadiazole (522 mg).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe resulting precipitate was collected by filtration
  3. washrinsed with water

Sources & evidence

ORD record
ord-5a38ef6cc2cd48e09ea0cb14ec319729
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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