Hydrochloric Acid → 2-Bromo-1,3-thiazole-4-carboxylic acid

HRID 1108282Notes

Reaction equation

HRID 1108282 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:11])[S:9][CH:10]=1)=[O:5])C.Cl>[OH-].[Na+]>[Br:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylate

Product 1

HCID 27632092-Bromo-1,3-thiazole-4-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a 100 mL 24/40 round bottom flask was charged 3.25 g (13.8 mmol) of 2-bromo-4-thiazolecarboxylic acid ethyl ester (Helv. Chim. Acta, 1942, 25, 1073) dissolved in 20 mL of 1N sodium hydroxide. The reaction was stirred at room temperature for 3 h, cooled down in an ice bath and acidified to pH 2 with SN hydrochloric acid. The white precipitate was filtered, washed with 20 mL cold water, and dried in a vacuum oven to give 2.7 g (94%) of 2-bromo-4-thiazolecarboxylic acid. m.p. 227-229° C., Rf =0.16 (20% methanol/chloroform). 1H NMR (300 MHz, DMSO-d6) δ 8.43 (s, 1H).

Workup

  1. temperaturecooled down in an ice bath
  2. filtrationThe white precipitate was filtered
  3. washwashed with 20 mL cold water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-b9ad7fbef84348f590ab16def957faf5
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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