4-Nitrophenol → 5-[(4-Nitrophenoxy)methyl]-3-phenyl-1,2,4-oxadiazole

HRID 733819Notes

Reaction equation

HRID 733819 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 9667145-(Chloromethyl)-3-phenyl-1,2,4-oxadiazole

Product 1

HCID 78942615-[(4-Nitrophenoxy)methyl]-3-phenyl-1,2,4-oxadiazoleYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Nitrophenol (0.36 g, 2.56 mmole), 5-(chloromethyl)-3-phenyl-1,2,4-oxadiazole (0.5 g, 2.56 mmole) and anhydrous K2CO3 (0.39 g, 2.82 mmole) were dissolved in anhydrous acetone (20 mL) and heated to reflux for 12 h. Reaction mixture was cooled and the solvent removed under vacuum. The crude solid formed was collected by filtration, washed with water and dried under vacuum to provide 5-[(4-nitrophenoxy)methyl]-3-phenyl-1,2,4-oxadiazole (0.70 g, 92%). 1H NMR (CDCl3): δ 8.25 (d, 2H, J=8.8 Hz), 8.08 (dd, 2H, J=8.2 Hz), 7.52–7.49 (m, 3H), 7.13 (d, 2H, J=8.8 Hz), 5.45 (s, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. customReaction mixture
  4. temperaturewas cooled
  5. customthe solvent removed under vacuum
  6. customThe crude solid formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-7f1240fc09334533a8ef918df69c4764
Source dataset
uspto-grants-2009_09
Patent number
US07589200B2

Reaction notes

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