Sodium Hydroxide → 4-(Trifluoromethyl)Thiazole-5-Carboxylic Acid

HRID 389088Notes

Reaction equation

HRID 389088 reaction equation
[OH-].[Na+].[F:3][C:4]([F:16])([F:15])[C:5]1[N:6]=[CH:7][S:8][C:9]=1[C:10]([O:12]CC)=[O:11]>C(O)C>[F:16][C:4]([F:3])([F:15])[C:5]1[N:6]=[CH:7][S:8][C:9]=1[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135933995-Thiazolecarboxylic acid, 4-(trifluoromethyl)-, ethyl ester

Product 1

HCID 189433734-(Trifluoromethyl)Thiazole-5-Carboxylic AcidYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous sodium hydroxide solution (2 ml) was added to a solution of ethyl 4-(trifluoromethyl)-1,3-thiazole-5-carboxylate (301 mg) in ethanol (3 ml), followed by stirring at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure and water was added thereto, followed by washing with diethylether. A 1M hydrochloric acid (2 ml) was added to the aqueous layer, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain 4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid (261 mg) as a light brown solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure and water
  2. additionwas added
  3. washby washing with diethylether
  4. additionA 1M hydrochloric acid (2 ml) was added to the aqueous layer
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-901215f9323249abad37b22f8e7bd8ca
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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