Hydrochloric Acid → 2-Aminothiazole-4-carboxylic acid

HRID 244658Notes

Reaction equation

HRID 244658 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9]CC)=[O:8])[N:6]=1.Cl>O1CCOCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 73216Ethyl 2-aminothiazole-4-carboxylate

Product 1

HCID 15018822-Aminothiazole-4-carboxylic acidYield 119.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2-amino-1,3-thiazole-4-carboxylate (150 mg) (for example available, from Maybridge Chemical Company) in 1,4-dioxane (3 ml) was added 2M hydrochloric acid (2 ml) and the mixture heated at reflux under nitrogen for 70 h. The mixture was cooled to room temperature and the solvent removed in vacuo. Toluene (15 ml) was added and the solvent removed in vacuo to give a solid that was dried in an vacuum oven overnight to give the title compound (150 mg) as a brown solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux under nitrogen for 70 h
  3. customthe solvent removed in vacuo
  4. additionToluene (15 ml) was added
  5. customthe solvent removed in vacuo
  6. customto give a solid
  7. customthat was dried in an vacuum oven overnight

Sources & evidence

ORD record
ord-bb195289752f4faaa9ff5bf8e074e332
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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