Pyridine → HCID 22934545, compound

HRID 1354451Notes

Reaction equation

HRID 1354451 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]1([C:20]2NN=[N:22][N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>O>[C:14]1([C:20]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:22][N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 178418369HCID 178418369, compound

Product 1

HCID 22934545HCID 22934545, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-chloroformylbenzoate (6.81 g), 5-phenyl-1H-tetrazole (5.01 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-phenyl-1,3,4-oxadiazol-2-yl)benzoate (7.88 g, yield 82%). Recrystallization from hexane-tetrahydrofuran gave colorless crystals. melting point: 172–173° 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-2b35967d4f6342bbb4b28c8826484642
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

Loading…