Hydrochloric Acid → 2-(3-Methylphenyl)-5-methyl-1,3-thiazole-4-carboxylic acid

HRID 1816629Notes

Reaction equation

HRID 1816629 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([CH3:17])=[C:11]([C:13]([O:15]C)=[O:14])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([CH3:17])=[C:11]([C:13]([OH:15])=[O:14])[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22494233Methyl 2-(3-methylphenyl)-5-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 224942712-(3-Methylphenyl)-5-methyl-1,3-thiazole-4-carboxylic acidYield 106%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 g of methyl 2-(3-methylphenyl)-5-methyl-1,3-thiazole-4-carboxylate was dissolved in 10 ml methanol, 1 ml of 5N sodium hydroxide was added, and the mixture was heated under reflux for 1 hour. The reaction solution was ice-cooled and neutralized with 2N hydrochloric acid, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated, to give 0.2 g of 2-(3-methylphenyl)-5-methyl-1,3-thiazole-4-carboxylic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. extractionby extracting with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6d52dc9521eb40719a0ddea0b6e011ed
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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