Hydrochloric Acid → HCID 21105743, compound

HRID 1354469Notes

Reaction equation

HRID 1354469 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[C:14]1[O:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[N:17][N:18]=1)[C:7]([O:9]C)=[O:8])([O-:3])=[O:2].[OH-].[Na+].Cl>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[C:14]1[O:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[N:17][N:18]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22934563HCID 22934563, compound

Product 1

HCID 21105743HCID 21105743, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-nitro-4-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoate (2.00 g), 1 M aqueous sodium hydroxide solution (10 ml) and tetrahydrofuran (10 ml) was heated under reflux for 1 hr. After cooling, 1 M hydrochloric acid was added to acidify the reaction mixture. The crystals were collected by filtration and dissolved in ethyl acetate-tetrahydrofuran. This solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 3-nitro-4-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (1.20 g, yield 62%). Recrystallization from hexane-tetrahydrofuran gave pale-yellow prism crystals. melting point: 254–255° 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-tetrahydrofuran
  6. washThis solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-84b18c1ea4c4484e8edc58e2c052676f
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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