Phosphorus oxychloride → 4-[5-(3-Iodo-benzyl)-[1,3,4]oxadiazol-2-yl]-benzonitrile

HRID 1468165Notes

Reaction equation

HRID 1468165 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=O)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)(Cl)=O>>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][C:9]1[O:22][C:13]([C:14]2[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=2)=[N:12][N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 675080464-cyano-benzoic acid N'-[2-(3-iodo-phenyl)-acetyl]-hydrazide

Product 1

HCID 675153214-[5-(3-Iodo-benzyl)-[1,3,4]oxadiazol-2-yl]-benzonitrileYield 77.7%

Conditions

Temperature
110 °C

Procedure

Suspend 4-cyano-benzoic acid N′-[2-(3-iodo-phenyl)-acetyl]-hydrazide (0.50 g, 1.23 mmol) in phosphorous oxychloride (2.00 mL, 21.0 mmol) and heat at 110° C. for 1 h, resulting in complete dissolution. Cool the mixture to room temperature, pour into ice water and stir until all of the ice melts resulting in a solid precipitate. Collect the formed solid by filtration, wash with H2O and dry on the filter pad to provide 0.37 g 77% yield of 4-[5-(3-iodo-benzyl)-[1,3,4]oxadiazol-2-yl]-benzonitrile as a powder.

Workup

  1. customresulting in complete dissolution
  2. temperatureCool the mixture to room temperature
  3. custommelts resulting in a solid precipitate
  4. customCollect the formed solid
  5. filtrationby filtration
  6. washwash with H2O
  7. customdry on the filter pad

Sources & evidence

ORD record
ord-8c25ce76574d420f8b6940d0a5c08cc4
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

Loading…