Potassium Hydroxide → 4-Phenylthiazole-2-carboxylic acid

HRID 2380758Notes

Reaction equation

HRID 2380758 reaction equation
C([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)=[O:5])C.[OH-].[K+]>CO>[C:11]1([C:9]2[N:10]=[C:6]([C:4]([OH:5])=[O:3])[S:7][CH:8]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 24730326Ethyl 4-phenyl-1,3-thiazole-2-carboxylate

Product 1

HCID 38785394-Phenylthiazole-2-carboxylic acidYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-phenyl-thiazole-2-carboxylic acid ethyl ester (282 mg, 1.21 mmol) dissolved in methanol (10 ml) was added 1N—KOH (3.63 ml, 3.63 mmol) and the mixture was allowed to react at 60° C. for 15 minutes. After the solvent was evaporated from the reaction mixture, the residue was dissolved by adding water and acidified (pH=2) with 2N—HCl under ice cooling. The produced precipitates were filtered with suction, washed with water and recrystallized from methanol-water to afford 190 mg (yield 72%) of the desired 4-phenyl-thiazole-2carboxylic acid as white solids.

Workup

  1. customto react at 60° C. for 15 minutes
  2. customAfter the solvent was evaporated from the reaction mixture
  3. dissolutionthe residue was dissolved
  4. additionby adding water
  5. customThe produced precipitates
  6. filtrationwere filtered with suction
  7. washwashed with water
  8. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-c05d27514d6d42968b618997d8093e32
Source dataset
uspto-grants-2012_09
Patent number
US08257931B2

Reaction notes

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