Boron trifluoride etherate → 3-(2-Dimethylaminophenylthiomethyl)-1,2,4-oxadiazole

HRID 848169Notes

Reaction equation

HRID 848169 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:10][C:11](=[N:13][OH:14])[NH2:12].[CH2:16](OC(OCC)OCC)C.B(F)(F)F.CCOCC>>[CH3:1][N:2]([CH3:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:10][C:11]1[N:12]=[CH:16][O:14][N:13]=1

Participants

4

Reactant 3

HCID 8000Boron trifluoride etherateHCID 31214Ethyl orthoformateHCID 541832962-(2-Dimethylaminophenylthio)acetamidoxime

Product 1

HCID 205663423-(2-Dimethylaminophenylthiomethyl)-1,2,4-oxadiazole

Procedure

A mixture of 2-(2-dimethylaminophenylthio)acetamidoxime (1.0 g), triethylorthoformate (1.5 ml) and boron trifluoride etherate (0.015 ml) was warmed at 70° whence a solution soon formed. Heating at 70° was continued for 5 hours, the reaction mixture cooled and solvent removed by evaporation under reduced pressure. The residual oil was taken up in diethyl ether, washed with 5% aqueous sodium carbonate solution and water, dried and evaporated to dryness under reduced pressure. The residue was distilled under reduced pressure to give 3-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole as a colourless oil, b.p. 119° (0.07 mm Hg).

Workup

  1. temperaturewas warmed at 70° whence a solution
  2. customsoon formed
  3. temperatureHeating at 70°
  4. temperaturethe reaction mixture cooled
  5. customsolvent removed by evaporation under reduced pressure
  6. washwashed with 5% aqueous sodium carbonate solution and water
  7. customdried
  8. customevaporated to dryness under reduced pressure
  9. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-69f9fef448a24feb8765b4eb8ad06143
Source dataset
uspto-grants-1981_10
Patent number
US04294843

Reaction notes

Loading…