Ethanol → HCID 22934560, compound

HRID 1354459Notes

Reaction equation

HRID 1354459 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)=[N:12][N:11]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[CH2:29](O)[CH3:30]>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([O:21][CH2:29][CH3:30])=[O:20])=[CH:17][CH:16]=2)=[N:12][N:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 21105753HCID 21105753, compound

Product 1

HCID 22934560HCID 22934560, compoundYield 24%

Procedure

A mixture of 4-[5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (2.00 g), conc. sulfuric acid (0.5 ml) and ethanol (50 ml) was heated under reflux for 6 hrs. After cooling, the reaction mixture was concentrated, and the residue was diluted with ethyl acetate. This solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1, volume ratio) to give ethyl 4-[5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl]benzoate (0.51 g, yield 24%). Recrystallization from hexane-ethyl acetate gave pale-yellow prism crystals. melting point: 127–128° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hrs
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated
  5. additionthe residue was diluted with ethyl acetate
  6. washThis solution was washed with saturated aqueous sodium hydrogen carbonate solution 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=4:1-2:1, volume ratio)

Sources & evidence

ORD record
ord-1220f5a9c73d4a42bacac348bb0ce194
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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