Hydrochloric Acid → 5-Isopropyl-2-methylthiazole-4-carboxylic acid

HRID 244625Notes

Reaction equation

HRID 244625 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH:12]([CH3:14])[CH3:13])=[C:5]([C:7]([O:9]CC)=[O:8])[N:6]=1.Cl>O1CCOCC1.Cl>[CH3:1][C:2]1[S:3][C:4]([CH:12]([CH3:14])[CH3:13])=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58356351Ethyl 2-methyl-5-(1-methylethyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 150939445-Isopropyl-2-methylthiazole-4-carboxylic acidYield 98.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-methyl-5-(1-methylethyl)-1,3-thiazole-4-carboxylate (200 mg) was dissolved in 1,4-dioxane (2 ml). Hydrochloric acid (2 ml) was added and the mixture was heated at reflux under nitrogen for 18 h. One drop of concentrated hydrochloric acid was added and the mixture was heated at reflux for 72 h. The mixture was cooled to RT, the solvent was removed in vacuo and toluene (15 ml) was added. The solvent was removed in vacuo to give a brown oil which solidified on standing. The product was dried in a vacuum oven overnight to give the title compound (171 mg) as a brown solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen for 18 h
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 72 h
  5. customthe solvent was removed in vacuo and toluene (15 ml)
  6. additionwas added
  7. customThe solvent was removed in vacuo
  8. customto give a brown oil which
  9. customThe product was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-a67bd060ef314631bd504549663bad36
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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