Hydrochloric Acid → HCID 58542567, compound

HRID 1843105Notes

Reaction equation

HRID 1843105 reaction equation
[F:1][C:2]([F:21])([C:7]1[S:8][C:9]([C:16]([O:18]CC)=[O:17])=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=1)[C:3]([F:6])([F:5])[F:4].[OH-].[Na+].Cl>CO.O>[F:21][C:2]([F:1])([C:7]1[S:8][C:9]([C:16]([OH:18])=[O:17])=[C:10]([C:12]([F:14])([F:15])[F:13])[N:11]=1)[C:3]([F:6])([F:5])[F:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58542500HCID 58542500, compound

Product 1

HCID 58542567HCID 58542567, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 540 mg (1.57 mmol) of ethyl 2-(pentafluoroethyl)-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate in 3 ml of methanol and 1 ml of water is admixed with 94.4 mg (2.36 mmol) of sodium hydroxide solution and heated at 60° C. for two hours. The reaction mixture is acidified with conc. hydrochloric acid and extracted four times with dichloromethane, and the organic phase is washed with saturated sodium chloride solution, dried over magnesium sulphate and, after filtration, is concentrated by evaporation. This gives 417 mg (min. 50% strength, max. 82%) of 2-(pentafluoroethyl)-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid.

Workup

  1. extractionextracted four times with dichloromethane
  2. washthe organic phase is washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationafter filtration
  5. concentrationis concentrated by evaporation

Sources & evidence

ORD record
ord-352b0ef74d7644bcbf4904b09a2503b9
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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