Potassium Hydroxide → 4-(4-Methylphenyl)-1,3-thiazole-2-carboxylic acid

HRID 1708945Notes

Reaction equation

HRID 1708945 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]([O:15]CC)=[O:14])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:13]([OH:15])=[O:14])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14772720Ethyl 4-(4-methylphenyl)-1,3-thiazole-2-carboxylate

Product 1

HCID 147727214-(4-Methylphenyl)-1,3-thiazole-2-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-(4-methylphenyl)-2-thiazolecarboxylate (300 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 distilled off 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-(4-methylphenyl)-2-thiazolecarboxylic acid as white solids, m.p. 112°-114° C.

Workup

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

Sources & evidence

ORD record
ord-9db69e64efe946868adb493de727e972
Source dataset
uspto-grants-1990_08
Patent number
US04946855

Reaction notes

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