Cyanogen Bromide → HCID 14951345, compound

HRID 2211183Notes

Reaction equation

HRID 2211183 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([NH:14][NH2:15])=[O:13])[CH:6]=[CH:7][CH:8]=1.C(=O)(O)[O-].[Na+].[N:27]#[C:28]Br>O1CCOCC1.O>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]2[O:13][C:28]([NH2:27])=[N:15][N:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 131678272-[(3-Trifluoromethylphenyl)amino]benzoic acid hydrazide

Product 1

HCID 14951345HCID 14951345, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a room temperature solution of 2-[(3-trifluoromethylphenyl)amino]benzoic acid hydrazide (532.7 mg, 1.81 mmoles) in 5 ml of dioxane is added sodium bicarbonate (155.0 mg, 1.84 mmoles) in 5 ml of water. After stirring at room temperature for five minutes, cyanogen bromide (192.0 mg, 1.81 mmoles) is added, and stirring is continued for 2.5 hours. The tan precipitate is removed by filtration and washed with 10 ml of 50% aqueous dioxane. Drying in vacuo provides 398.0 mg (69%) of 5-[2-[[3-(trifluoromethyl)phenyl]amino]phenyl]-1,3,4-oxadiazol-2-amine, mp 185°-187° C.

Workup

  1. stirringstirring
  2. waitis continued for 2.5 hours
  3. customThe tan precipitate is removed by filtration
  4. washwashed with 10 ml of 50% aqueous dioxane
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-8f741bdf79d542c8a3b122b598a485b9
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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