4-Nitrophenol → HCID 7894261, compound

HRID 405336Notes

Reaction equation

HRID 405336 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 7894261HCID 7894261, compoundYield 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-f2ad74318d204aaf81717f5eb1b8b0ba
Source dataset
uspto-grants-2014_06
Patent number
US08748597B2

Reaction notes

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