Hydrochloric Acid → 2-Bromothiazole-5-carboxylic acid

HRID 1108287Notes

Reaction equation

HRID 1108287 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([Br:11])=[N:8][CH:7]=1)=[O:5])C.Cl>[OH-].[Na+]>[Br:11][C:9]1[S:10][C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

Product 1

HCID 27632102-Bromothiazole-5-carboxylic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a 100 mL 14/20 round bottom flask was charged 2.4 g (10.1 mmol) of 2-bromo-5-thiazolecarboxylic acid ethyl ester dissolved in 14 mL of 1N sodium hydroxide. The reaction was stirred at room temperature for 1.5 hours The yellow solution was acidified with SN hydrochloric acid to pH 2. The solid which formed was cooled in an ice bath, filtered, washed with water, and dried in a vacuum oven at 60° C. to give 1.9 g (90%) of 2-bromo-5-thiazolecarboxylic acid m.p. 185-186° C. (dec) as a white solid. Rf =0.12 (20% methanol/chloroform). 1H NMR (300 MHz, DMSO d6) δ 8.19(s, 1H).

Workup

  1. customThe solid which formed
  2. temperaturewas cooled in an ice bath
  3. filtrationfiltered
  4. washwashed with water
  5. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-2d63d789c5d14d63a8635964709a8da8
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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