Ethyl orthoformate → HCID 19703162, compound

HRID 861421Notes

Reaction equation

HRID 861421 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[N:8][OH:9])[NH2:7])=[CH:4][CH:3]=1.[CH2:12](OC(OCC)OCC)C>>[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:7]=[CH:12][O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 4429393N-Hydroxy-4-iodo-benzamidine

Product 1

HCID 19703162HCID 19703162, compound

Procedure

A mixture of 4-iodobenzamidoxime (3.93 g) in triethylorthoformate (15 ml) was heated at reflux for 4 hours. The mixture was evaporated and the residue was purified by flash column chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent to give 3-(4-iodophenyl)-1,2,4-oxadiazole (0.74 g) as a solid; NMR(CDCl3): 7.85(4H,s) and 8.74(1H,s); m/z 272(M).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe mixture was evaporated
  4. customthe residue was purified by flash column chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-0de3a0f8cbdd482989fa1ad6bebc3c27
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

Loading…