Furfural → Benzoxazole, 2-(2-furanyl)-5-nitro-

HRID 1287660Notes

Reaction equation

HRID 1287660 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].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=O>C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]2[O:10][C:17]([C:13]3[O:12][CH:16]=[CH:15][CH:14]=3)=[N:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7362FurfuralHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 3285015Benzoxazole, 2-(2-furanyl)-5-nitro-Yield 43.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Step A - 15.4 g of 4-nitro-2-aminophenol is dissolved in 250 ml of ethanol and to this solution 9.6 g of furaldehyde is added at room temperature. The reaction is allowed to stir at room temperature for 0.25 hr and the precipitated crystals are collected. The resulting Schiff Base is then dissolved in 250 ml of glacial acetic acid, treated with 44 g of lead tetraacetate and then refluxed for 2 hr. The mixture is then diluted with 250 ml of water and the precipitated product is collected and washed with water. Recrystallization from 150 ml of CH2Cl2 yields 10.1 g of 5-nitro-2-(2-furyl)benzoxazole, mp 175°-177°.

Workup

  1. additionis added at room temperature
  2. customthe precipitated crystals are collected
  3. dissolutionThe resulting Schiff Base is then dissolved in 250 ml of glacial acetic acid
  4. additiontreated with 44 g of lead tetraacetate
  5. temperaturerefluxed for 2 hr
  6. additionThe mixture is then diluted with 250 ml of water
  7. customthe precipitated product is collected
  8. washwashed with water
  9. customRecrystallization from 150 ml of CH2Cl2

Sources & evidence

ORD record
ord-c811f3bb24a94eaa9730db654f7dd025
Source dataset
uspto-grants-1976_10
Patent number
US03985755

Reaction notes

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