Benzoyl chloride → HCID 622484, compound

HRID 1415129Notes

Reaction equation

HRID 1415129 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8](=[N:10][OH:11])[NH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14](Cl)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.B(F)(F)F.CCOCC>O1CCOCC1>[C:15]1([C:14]2[O:11][N:10]=[C:8]([C:7]3[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[N:9]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8000Boron trifluoride etherateHCID 3825473N-Hydroxy-4-nitrobenzimidamide

Product 1

HCID 622484HCID 622484, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 10.8 g. (0.06 mole) of p-nitrobenzamidoxime and 8.5 g. (0.06 mole) of benzoyl chloride in 250 ml. of dioxane is heated on a steam bath for one hour, followed by the addition of 2 ml. of BF3 -Et2O. After refluxing the solution overnight, the reaction mixture is cooled and the material which precipitates is collected by filtration to yield 8.1 g. (50%) of 5-phenyl-3-(4-nitrophenyl)-1,2,4-oxadizole.

Workup

  1. additionfollowed by the addition of 2 ml
  2. temperatureAfter refluxing the solution overnight
  3. temperaturethe reaction mixture is cooled
  4. customthe material which precipitates
  5. filtrationis collected by filtration
  6. customto yield 8.1 g

Sources & evidence

ORD record
ord-901ed1a1bcc743e1b1f1eb34e496da21
Source dataset
uspto-grants-1977_01
Patent number
US04003909

Reaction notes

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