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

HRID 2244403Notes

Reaction equation

HRID 2244403 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:11])[S:9][CH:10]=1)=[O:5])C.[OH-].[Na+]>CO>[CH3:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=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 acidYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-methyl-thiazole-4-carboxylic acid ethyl ester (3.14 g, 20.00 mmol) in methanol (50.00 ml) was treated with 2N NaOH (30.00 ml) and stirred at room temperature for 45 min. Methanol was removed in vacuo and the resulting slurry was neutralized with HCl 2N (30.00 ml). The aqueous phase was then extracted three times with ethyl acetate. The combined organic layers were dried with sodium sulphate and evaporated. 2-Methyl-thiazole-4-carboxylic acid (2.48 g, 87%) was obtained as a yellow solid, MS (ISP): m/e=142.1 (M−H), which was used crude.

Workup

  1. customMethanol was removed in vacuo
  2. extractionThe aqueous phase was then extracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried with sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-d98b5a37dd8342d8912738b4cf1a4856
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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