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

HRID 1753335Notes

Reaction equation

HRID 1753335 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-e3f36dc0f4c24b489610d6671c0c2209
Source dataset
uspto-grants-2015_10
Patent number
US09162989B2

Reaction notes

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