Hydrochloric Acid → 4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid

HRID 490710Notes

Reaction equation

HRID 490710 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH:21]([CH3:23])[CH3:22])=[O:5])C.[OH-].[Na+].Cl>C1COCC1>[CH:21]([C:7]1[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=2)[S:10][C:6]=1[C:4]([OH:5])=[O:3])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 587658244-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 589340934-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester (0.62 g, 1.80 mmol) in THF (10 mL) is added 5M NaOH (3.5 mL, 17.50 mmol). The mixture is heated at 70° C. for 12 h. Upon cooling to RT, the mixture is acidified with 5M HCl and extracted with EtOAc. The organics are washed with water and brine, and dried with MgSO4. After concentration, the title compound is obtained (0.46 g, 81%). The material is used without further purification.

Workup

  1. temperatureUpon cooling to RT
  2. extractionextracted with EtOAc
  3. washThe organics are washed with water and brine
  4. dry with materialdried with MgSO4
  5. concentrationAfter concentration

Sources & evidence

ORD record
ord-9667c60aea1d46ae8d21f8ef57d229a4
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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