Hydrochloric Acid → 5-Methyl-2-phenyl-1,3-thiazole-4-carboxylic acid

HRID 1816619Notes

Reaction equation

HRID 1816619 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15]CC)=[O:14].[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 150939465-Methyl-2-phenyl-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 138353045-Methyl-2-phenyl-1,3-thiazole-4-carboxylic acidYield 112.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.8 g of ethyl 5-methyl-2-phenyl-1,3-thiazole-4-carboxylate was dissolved in 10 ml ethanol. 2 ml of 5N sodium hydroxide was added thereto, followed by heating 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 0.8 g of 5-methyl-2-phenyl-1,3-thiazole-4-carboxylic-acid.

Workup

  1. temperatureby heating
  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-5fa4f8437cee45e5b499419383213ff7
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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