Boron trifluoride etherate → 3,5-Bis(2-chlorophenyl)-1,2,4-oxadiazole

HRID 1648881Notes

Reaction equation

HRID 1648881 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14](=[N:16]O)[NH2:15].B(F)(F)F.CCOCC>O1CCOCC1.ClCCl>[Cl:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]1[N:16]=[C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])[O:5][N:15]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 691102-Chlorobenzoyl chlorideHCID 37487062-chloro-N'-hydroxybenzene-1-carboximidamide

Product 1

HCID 7937013,5-Bis(2-chlorophenyl)-1,2,4-oxadiazoleYield 53.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Chlorobenzoyl chloride (2.6 g) was dissolved in dioxan (90 ml) and 2-chlorobenzamidoxime (2.5 g) was added with stirring, followed by boron trifluoride etherate (0.2 ml). The solution was heated at reflux for 18 hours and was run down. The product was taken up in dichloromethane, and the solution was washed successively with saturated aqueous sodium bicarbonate, water, and saturated sodium chloride solution. It was then dried over magnesium sulphate, run down and recrystallised from ethanol to yield 2.3 g of desired product, mp 91°-92° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 18 hours
  3. washthe solution was washed successively with saturated aqueous sodium bicarbonate, water, and saturated sodium chloride solution
  4. dry with materialIt was then dried over magnesium sulphate
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-f0a5c759afbf492aae02c5ff20d8c24a
Source dataset
uspto-grants-1983_11
Patent number
US04414221

Reaction notes

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