Pyridine → Methyl 4-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzoate

HRID 1354453Notes

Reaction equation

HRID 1354453 reaction equation
Cl[C:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)=[O:3].[C:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2NN=[N:26][N:25]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].N1C=CC=CC=1>O>[C:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[O:3][C:2]([C:4]3[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=3)=[N:26][N:25]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 178419015HCID 178419015, compound

Product 1

HCID 22934530Methyl 4-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzoateYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-chloroformylbenzoate (1.17 g), 5-(4-t-butylphenyl)-1H-tetrazole (1.00 g) and pyridine (10 ml) was heated under reflux for 1 hr. After cooling, water was added to the mixture. 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 cold hexane to give methyl 4-[5-(4-t-butylphenyl)-1,3,4-oxadiazol-2-yl]benzoate (1.51, yield 92%). Recrystallization from hexane-tetrahydrofuran gave colorless prism crystals. melting point: 210–211° 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 cold hexane

Sources & evidence

ORD record
ord-85b4e8b78b974d90a7e9276c1c60f5d2
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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