4-Nitrobenzaldehyde → 5-(4-Nitrophenyl)-1,3-oxazole

HRID 450096Notes

Reaction equation

HRID 450096 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].S([CH2:22][N+:23]#[C-:24])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[O:9][CH:24]=[N:23][CH:22]=2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanide

Product 1

HCID 27370685-(4-Nitrophenyl)-1,3-oxazoleYield 95.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-nitro benzaldehyde (500 mg, 3.31 mmol), tosylmethyl isocyanide (640 mg, 3.31 mmol) and potassium carbonate (1.37 g, 9.9 mmol) were heated to reflux in methanol (10 ml) for 2 hr. Evaporation of the solvent yielded a residue, which was diluted with water and extracted into ethyl acetate. The organic layer was washed with water and brine, dried and concentrated under reduced pressure to yield 5-(4-nitro-phenyl)-oxazole (600 mg, 95%) as solid.

Workup

  1. temperaturewere heated
  2. customEvaporation of the solvent
  3. customyielded a residue, which
  4. extractionextracted into ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c1b219113ff4d88a12cfe50bc156ee1
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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