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

HRID 356440Notes

Reaction equation

HRID 356440 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[N:9]=[C:10]([Cl:13])[S:11][CH:12]=1)=[O:7])C>C(O)C>[Cl:13][C:10]1[S:11][CH:12]=[C:8]([C:6]([OH:7])=[O:5])[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13106141Ethyl 2-chlorothiazole-4-carboxylate

Product 1

HCID 218030262-Chloro-1,3-thiazole-4-carboxylic acidYield 61.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of NaOH (1.9 g, 47.5 mmol) and ethyl-2-chloro-4-thiazolecarboxylate (7.6 g, 40 mmol) in 100 mL absolute ethanol was stirred at RT for 4 h. After that, ethanol was removed in vacuo and the residue was dissolved in water. The aq layer was washed with ether and then acidified with conc HCl. The solid was filtered and air dried to give 4 g of 2-chloro-4-thiazolecarboxylic acid.

Workup

  1. customAfter that, ethanol was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. washThe aq layer was washed with ether
  4. filtrationThe solid was filtered
  5. customair dried

Sources & evidence

ORD record
ord-a8762a94cad2465db75febb4a7a983fd
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Reaction notes

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