N-Phenylhydroxylamine → 4-(2-oxazolyl)-phenyl-N-phenylnitrone

HRID 457246Notes

Reaction equation

HRID 457246 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[C:14]1([NH:20][OH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[N+:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O-:21])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7518N-PhenylhydroxylamineHCID 226310004-(1,3-Oxazol-2-YL)benzaldehyde

Product 1

HCID 734451214-(2-oxazolyl)-phenyl-N-phenylnitroneYield 70.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 4-(2-oxazolyl)-benzaldehyde (1 eq., 6.3 gm) and N-phenyl-hydroxyamine (1 eq., 3.9 gm) was refluxed in ethanol (100 ml) for 30 minutes and concentrated to a volume of 50 ml. An equal amount (50 ml) of water was added and the mixture was cooled in a refrigerator at 5° C. overnight. White crystals were obtained, which were isolated by filtration and dried, producing 6.7 gm of 4-(2-oxazolyl)-phenyl-N-phenylnitrone.

Workup

  1. concentrationconcentrated to a volume of 50 ml
  2. additionAn equal amount (50 ml) of water was added
  3. customWhite crystals were obtained
  4. customwhich were isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-1e0403360d164e34aa36cffec8d4d38f
Source dataset
uspto-grants-2007_03
Patent number
US07186845B2

Reaction notes

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