Sodium Hydroxide → 2-Methyl-1,3-thiazole-4-carboxylic acid

HRID 1443106Notes

Reaction equation

HRID 1443106 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9]CC)=[O:8])[N:6]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 2847282-Methyl-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-methylthiazole-4-carboxylate (17.0 g, 99.3 mmol) was dissolved in 150 ml of methanol and 2N NaOH (150 ml, 300 mmol) was added. The reaction mixture was stirred for 2 hours at room temperature. Methanol was evaporated and the residue was acidified with 2N HCl to pH 2. The aqueous layer was extracted two times with ethyl acetate. The organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product (13.0 g, 91%) was used without any further purification for the next step.

Workup

  1. customMethanol was evaporated
  2. extractionThe aqueous layer was extracted two times with ethyl acetate
  3. dry with materialThe organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product (13.0 g, 91%) was used without any further purification for the next step

Sources & evidence

ORD record
ord-cfcd35f8b75944d489e5d2a346e77f4f
Source dataset
uspto-grants-2010_02
Patent number
US07659401B2

Reaction notes

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