Sulfuric Acid → HCID 21105752, compound

HRID 1354478Notes

Reaction equation

HRID 1354478 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-:25])=[O:24])=[N:15][N:16]=2)=[CH:8][CH:7]=1.S(=O)(=O)(O)O>CC(C)=O>[N+:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1[O:13][C:12]([C:9]2[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][CH:10]=2)=[N:16][N:15]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22934524HCID 22934524, compound

Product 1

HCID 21105752HCID 21105752, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-[4-(1,3-dioxolan-2-yl)phenyl]-5-(2-nitrophenyl)-1,3,4-oxadiazole (1.75 g), 0.5 M sulfuric acid (15 ml) and acetone (50 ml) was heated under reflux for 1 hr. After cooling, the reaction mixture was concentrated, and the residue was diluted with ethyl acetate. This solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1, volume ratio) to give 4-[5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl]benzaldehyde (1.37 g, yield 89%). Recrystallization from hexane-ethyl acetate gave pale-yellow prism crystals. melting point: 189–190° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated
  5. additionthe residue was diluted with ethyl acetate
  6. washThis solution was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1, volume ratio)

Sources & evidence

ORD record
ord-16c13c7a65654f708dfb351b70f9048a
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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