5-Methylfurfural → 2-(5-Methylfuran-2-yl)-5-nitro-1,3-benzoxazole

HRID 1576865Notes

Reaction equation

HRID 1576865 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[CH3:12][C:13]1[O:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>CCO.O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]2[O:10][C:17]([C:16]3[O:19][C:13]([CH3:12])=[CH:14][CH:15]=3)=[N:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 120975-MethylfurfuralHCID 36133892-Amino-4-NitrophenolHCID 178418268HCID 178418268, compound

Product 1

HCID 127819142-(5-Methylfuran-2-yl)-5-nitro-1,3-benzoxazoleYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7.70 g (0.05 mole) of 4-nitro-2-aminophenol and 5.50 g (0.05 mole) of 5-methylfurfural are dissolved in 400 ml of 95% EtOH and refluxed overnight. The ethanol is removed and the resulting dark red oil is recrystallized from CH3CN yielding golden plates of the Schiff Base, mp 190°-193°. This material is then dissolved in CH3CN (200 ml) by heating and 22.2 g (0.05 mole) of lead tetraacetate added. Heating is continued for 5 min and then solution is diluted with an equal volume of water. The dark brown precipitate is collected, washed with water and recrystallized from CH2Cl2 and Darco G-60 yielding 6.1 g of product (50%), mp 182°-184°.

Workup

  1. temperaturerefluxed overnight
  2. customThe ethanol is removed
  3. customthe resulting dark red oil is recrystallized from CH3CN yielding golden plates of the Schiff Base, mp 190°-193°
  4. dissolutionThis material is then dissolved in CH3CN (200 ml)
  5. temperatureby heating
  6. temperatureHeating
  7. customThe dark brown precipitate is collected
  8. washwashed with water
  9. customrecrystallized from CH2Cl2 and Darco

Sources & evidence

ORD record
ord-9ec96254051143a4b4c264571c4f0511
Source dataset
uspto-grants-1976_09
Patent number
US03983130

Reaction notes

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