Pyridine → HCID 22934524, compound

HRID 1354411Notes

Reaction equation

HRID 1354411 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[O:13]1[CH2:17][CH2:16][O:15][CH:14]1[C:18]1[CH:23]=[CH:22][C:21]([C:24]2NN=[N:26][N:25]=2)=[CH:20][CH:19]=1.N1C=CC=CC=1>O>[O:13]1[CH2:17][CH2:16][O:15][CH:14]1[C:18]1[CH:19]=[CH:20][C:21]([C:24]2[O:7][C:6]([C:5]3[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=3[N+:1]([O-:3])=[O:2])=[N:26][N:25]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 178420020HCID 178420020, compound

Product 1

HCID 22934524HCID 22934524, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-nitrobenzoyl chloride (0.190 g), 5-[4-(1,3-dioxolan-2-yl)phenyl]-1H-tetrazole (0.200 g) and pyridine (5 ml) was heated under reflux for 1 hr. After cooling, water was added to the reaction mixture, and the crystals were collected by filtration, and dissolved in ethyl acetate. This solution was washed with 1 M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with hexane to give 2-[4-(1,3-dioxolan-2-yl)phenyl]-5-(2-nitrophenyl)-1,3,4-oxadiazole (0.240 g, yield 77%). Recrystallization from hexane-ethyl acetate gave colorless prism crystals. melting point: 88–89° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. filtrationthe crystals were collected by filtration
  5. dissolutiondissolved in ethyl acetate
  6. washThis solution was washed with 1 M hydrochloric acid, water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-e59444aab72d48b9a9502a0b285f8ee1
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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