Hydrochloric Acid → [5-(4-Trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]benzoic acid

HRID 1354464Notes

Reaction equation

HRID 1354464 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]3[CH:23]=[CH:22][C:17](C(OC)=O)=[CH:16][CH:15]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1.[OH-:26].[Na+].[O:28]1[CH2:32]CCC1.Cl>O.CO>[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:22][C:23]=3[C:32]([OH:28])=[O:26])=[N:11][N:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22934538Methyl 4-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]benzoate

Product 1

HCID 21105763[5-(4-Trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]benzoic acidYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 4-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]benzoate (0.838 g), 1 M aqueous sodium hydroxide solution (5 ml), tetrahydrofuran (100 ml) and methanol (50 ml) was heated under reflux for 1 hr. After cooling, the reaction mixture was poured into water, and 1 M hydrochloric acid was added to acidify the mixture. The mixture was extracted with ethyl acetate-tetrahydrofuran (1:1, volume ratio). The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from tetrahydrofuran to give 4 [5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]benzoic acid (0.672 g, yield 83%) as a colorless crystalline powder. melting point: >300° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate-tetrahydrofuran (1:1, volume ratio)
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-438ff29fa68b4c3db8d91591c939af7d
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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