Sodium Hydroxide → 5-(1-Methylethyl)-4-thiazolecarboxylic acid

HRID 244668Notes

Reaction equation

HRID 244668 reaction equation
[CH3:1][CH:2]([C:4]1[S:8][CH:7]=[N:6][C:5]=1[C:9]([O:11]C)=[O:10])[CH3:3].[OH-].[Na+]>CO>[CH3:3][CH:2]([C:4]1[S:8][CH:7]=[N:6][C:5]=1[C:9]([OH:11])=[O:10])[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13015587Methyl 5-isopropylthiazole-4-carboxylate

Product 1

HCID 225730545-(1-Methylethyl)-4-thiazolecarboxylic acidYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 5-(1-methylethyl)-1,3-thiazole-4-carboxylate (1.9 g) in methanol (20 ml) was added 2M sodium hydroxide (20 ml) and the mixture stirred at 20° C. for 18 h. The solvent was removed in vacuo and the residue taken up in water (20 ml) and acidified to pH=2 using 2M hydrochloric acid. The mixture was extracted with ethyl acetate (100 ml), dried over sodium sulphate and evaporated in vacuo to give the title compound (1.7 g) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionThe mixture was extracted with ethyl acetate (100 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-6b83f6d9aaa045038bfc47988077297a
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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