Hydrochloric Acid → 2-[4-(Trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylic acid

HRID 2363202Notes

Reaction equation

HRID 2363202 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=2)=[CH:5][CH:4]=1.[Li+].[OH-].Cl>C1COCC1.O>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 210512492-(4-Trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 433335812-[4-(Trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Ethyl 2-[4-(trifluoromethyl)phenyl]thiazole-5-carboxylate (28 mg, 0.09 mmol.) and LiOH (5.0 mg, 0.12 mmol) were diluted with THF/H2O=1:1 (1 mL), and then stirred for 3 hrs at room temperature. The mixture was acidified with 1N HCl, concentrated under reduced pressure, and diluted with EtOAc and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to yield the crude title compound as a yellow solid (23 mg, 91%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac3000b0c24e453cb2cff2ddde2c53e7
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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