Potassium Hydroxide → 2-Chloro-1,3-thiazole-4-carboxylic acid

HRID 573522Notes

Reaction equation

HRID 573522 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([Cl:11])[S:9][CH:10]=1)=[O:5])C.[OH-].[K+]>C(O)C.O.O>[Cl:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 13106141Ethyl 2-chlorothiazole-4-carboxylate

Product 1

HCID 218030262-Chloro-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

14.0 g (73.1 mmol) of 2-chlorothiazole-4-carboxylic acid ethyl ester were slowly added to a solution of 11.0 g (0.17 mol, 85% purity) of potassium hydroxide in ethanol/water (1:3, 200 ml) at 0° C. The reaction mixture was stirred at room temperature for 16 h, diluted with water and washed twice with diethyl ether. The aqueous layer was acidified (pH=5.5) with conc. HCl and stirred at room temperature for three days. The formed precipitate was collected by filtration and dried at 40° C. under vacuum to yield 7.0 g (56%, 95% purity) of the title compound as a brown solid.

Workup

  1. washwashed twice with diethyl ether
  2. stirringstirred at room temperature for three days
  3. filtrationThe formed precipitate was collected by filtration
  4. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-eac81ee8ecdb415c8b6a241769cb0af2
Source dataset
uspto-grants-2015_05
Patent number
US09029639B2

Reaction notes

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