4-Nitrobenzaldehyde → 5(4H)-Oxazolone, 2-methyl-4-[(4-nitrophenyl)methylene]-

HRID 1692167Notes

Reaction equation

HRID 1692167 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([NH:15][CH2:16][C:17]([OH:19])=[O:18])(=O)[CH3:13].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>>[CH3:13][C:12]1[O:19][C:17](=[O:18])[C:16](=[CH:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:15]=1

Participants

5

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 517045Sodium Acetate

Product 1

HCID 3644985(4H)-Oxazolone, 2-methyl-4-[(4-nitrophenyl)methylene]-Yield 66.5%

Conditions

Temperature
120 °C

Procedure

4-Nitrobenzaldehyde (53.7 g, 0.356 mol), N-acetylglycine (49.9 g, 0.427 mol) and sodium acetate (37.9 g, 0.463 mol) were mixed with acetic anhydride (168 g, 1.78 mol) and the resulting mixture heated with stirring to 120° C. for 6 hrs, giving a dark suspension. The mixture was then cooled to RT overnight, resulting in the formation of a precipitated solid. The reaction mixture was poured into ice-water (150 g) and the resulting suspended solid was collected by filtration. The crude solid product was washed with acetone (100 ml) then recrystallized from hot acetone (650 ml) to give a crystalline solid that was washed with 50% aqueous ethanol, then dried in vacuo to give 2-methyl-4-(4-nitrobenzylidene)oxazol-5(4H)-one (55.0 g, 66%) as pale yellow needles. The crystallisation mother liquors and washes were combined and evaporated to give a solid residue that was recrystallized from acetone to give a second crop of 2-methyl-4-(4-nitrobenzylidene)oxazol-5(4H)-one (8 g, 10%). The combined yield of 2-methyl-4-(4-nitrobenzylidene)oxazol-5(4H)-one was 63 g (76%)

Workup

  1. temperaturethe resulting mixture heated
  2. customgiving a dark suspension
  3. temperatureThe mixture was then cooled to RT overnight
  4. customresulting in the formation of a precipitated solid
  5. filtrationwas collected by filtration
  6. washThe crude solid product was washed with acetone (100 ml)
  7. customthen recrystallized from hot acetone (650 ml)
  8. customto give a crystalline solid
  9. washthat was washed with 50% aqueous ethanol
  10. customdried in vacuo

Sources & evidence

ORD record
ord-e6de5bf245744dbfb98c920214ca39c0
Source dataset
uspto-grants-2012_04
Patent number
US08153841B2

Reaction notes

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