Benzonitrile → HCID 19899506, compound

HRID 1030301Notes

Reaction equation

HRID 1030301 reaction equation
[Na].S([O-])([O-])(=O)=O.O[NH3+:8].O[NH3+].C(=O)([O-])[O-].[Na+].[Na+].[Br:17][C:18]1[CH:29]=[C:22]2[C:23]([O:25]C(=O)[NH:27][C:21]2=[CH:20][CH:19]=1)=O.[C:30](#[N:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([NH2:27])=[C:22]([C:23]2[O:25][N:8]=[C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:37]=2)[CH:29]=1

Participants

7

Reactant 5

HCID 7505BenzonitrileHCID 10340Sodium CarbonateHCID 24846Hydroxylamine sulfateHCID 2885615-Bromoisatoic AnhydrideHCID 5360545Sodium

Product 1

HCID 19899506HCID 19899506, compoundYield 145.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

48 g of benzonitrile and 3 g of an anionic surfactant (sodium salt of sulfonated N,N-dibutyloleamide) were dispersed in 150 ml of water at room temperature in the course of an hour. 39.2 g of hydroxylammonium sulfate were added, followed by 27 g of sodium carbonate added a little at a time. The reaction was heated to 90° C., stirred at that temperature for five hours and then cooled back to 60° C. 112 g of 5-bromoisatoic anhydride was then added, and the mixture was again heated to 90° C. After two hours' stirring at that temperature, the product was filtered off with suction, washed and redispersed in 1200 ml of water. The pH was adjusted to 10.5-11.0 with 50% strength by weight sodium hydroxide solution, the mixture was stirred at that temperature for one hour and then filtered with suction. The filter residue was washed with water and dried, leaving 110 g of 4-bromo-2-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline in a very finely divided crystal form.

Workup

  1. additionadded a little at a time
  2. temperaturecooled back to 60° C
  3. temperaturethe mixture was again heated to 90° C
  4. stirringAfter two hours' stirring at that temperature
  5. filtrationthe product was filtered off with suction
  6. washwashed
  7. additionredispersed in 1200 ml of water
  8. stirringthe mixture was stirred at that temperature for one hour
  9. filtrationfiltered with suction
  10. washThe filter residue was washed with water
  11. customdried

Sources & evidence

ORD record
ord-15815f2fe4794f09acab2e7c9daf465f
Source dataset
uspto-grants-1992_04
Patent number
US05104991

Reaction notes

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