Potassium Hydroxide → [2-(2,2,2-Trifluoroacetamido)-1,3-thiazol-4-yl]acetic acid

HRID 127106Notes

Reaction equation

HRID 127106 reaction equation
[OH-].[K+].[F:3][C:4]([F:20])([F:19])[C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([O:16]CC)=[O:15])[N:12]=1)=[O:6]>O>[F:20][C:4]([F:3])([F:19])[C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=1)=[O:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 2303713T0501-6206

Product 1

HCID 20288638[2-(2,2,2-Trifluoroacetamido)-1,3-thiazol-4-yl]acetic acidYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of potassium hydroxide (4.2 g.) in water (100 ml.) was added ethyl 2-trifluoroacetamidothiazol-4-ylacetate (14.1 g.) at room temperature with stirring, and the mixture was stirred for 1 hour at room temperature. After the reaction, the reaction mixture was washed with ethyl acetate and adjusted to about pH 3 with 10% hydrochloric acid under ice-cooling and stirring. The precipitated solid was collected by filtration and dried over phosphorus pentoxide to give 2-trifluoroacetamidothiazol-4-ylacetic acid (8.5 g.), mp 117°-120° C.

Workup

  1. stirringthe mixture was stirred for 1 hour at room temperature
  2. customAfter the reaction
  3. washthe reaction mixture was washed with ethyl acetate
  4. temperaturecooling
  5. stirringstirring
  6. filtrationThe precipitated solid was collected by filtration
  7. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-b0cafa0395c9484f8220e7fb4a5ce7ef
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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