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

HRID 1939041Notes

Reaction equation

HRID 1939041 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-897bcf9fbfbe4b34abd3db9009626991
Source dataset
uspto-grants-1997_12
Patent number
US05693667

Reaction notes

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