Pyridine → HCID 22934523, compound

HRID 1354452Notes

Reaction equation

HRID 1354452 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].[F:14][C:15]([F:28])([F:27])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2NN=[N:24][N:23]=2)=[CH:18][CH:17]=1.N1C=CC=CC=1>O>[F:14][C:15]([F:27])([F:28])[C:16]1[CH:17]=[CH:18][C:19]([C:22]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:24][N:23]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 178506124HCID 178506124, compound

Product 1

HCID 22934523HCID 22934523, compoundYield 3,487.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-chloroformylbenzoate (1.39 g), 5-(4-trifluoromethylphenyl)-1H-tetrazol (1.50 g) and pyridine (30 ml) was heated under reflux for 1 hr. After cooling, water was added to the mixture. The crystals were collected by filtration and purified by silica gel column chromatography (hexane:tetrahydrofuran=1:9, volume ratio) to give methyl 4-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoate (1. 85 g, yield 76%). Recrystallization from hexane-ethyl acetate gave colorless prism crystals. melting point: 216–217° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. filtrationThe crystals were collected by filtration
  5. custompurified by silica gel column chromatography (hexane:tetrahydrofuran=1:9, volume ratio)

Sources & evidence

ORD record
ord-0699a6aa235d4688b521278d93fc7ae1
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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