Hydrochloric Acid → HCID 21105759, compound

HRID 1354455Notes

Reaction equation

HRID 1354455 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>O1CCCC1>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22934523HCID 22934523, compound

Product 1

HCID 21105759HCID 21105759, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoate (0.800 g), 1 M aqueous sodium hydroxide solution (4.6 ml) and tetrahydrofuran (5 ml) was heated under reflux for 1.5 hrs. After cooling, 1 M hydrochloric acid was added to acidify the mixture. The crystals were collected by filtration to give 4-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (0.71 g, yield 92%). Recrystallization from hexane-ethyl acetate gave colorless prism crystals. melting point: >300° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hrs
  3. temperatureAfter cooling
  4. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-77f3a0d137524993ae11f96ae784c58b
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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