Potassium Permanganate → 2,4-Dibromo-1,3-thiazole-5-carboxylic acid

HRID 1785478Notes

Reaction equation

HRID 1785478 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[Br:7][C:8]1[S:9][C:10]([CH:14]=[O:15])=[C:11]([Br:13])[N:12]=1>O>[Br:7][C:8]1[S:9][C:10]([C:14]([OH:2])=[O:15])=[C:11]([Br:13])[N:12]=1

Participants

4

Reactant 2

HCID 516875Potassium Permanganate2×HCID 36928392,4-Dibromo-1,3-thiazole-5-carbaldehyde

Product 1

HCID 151419582,4-Dibromo-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solid potassium permanganate (2.19 g, 13.85 mmol) was added portionwise to a hot suspension of 2,4-dibromo-thiazole-5-carbaldehyde (2.5 g, 9.23 mmol) in water (20 ml). The progress of the reaction was monitored by HPLC. More potassium permanganate was added until all of the aldehyde was consumed. The dark suspension was filtered while hot. The filtrate was cooled and acidified with conc. hydrochloric acid to pH=2 to 3. The resulting precipitate was filtered off to afford a white solid as the desired product. The filtrate was lyophilized and methanol was added to dissolve the remaining acid product. The suspension was filtered and the filtrate was concentrated in vacuo. Two crops were combined to give 2,4-dibromo-thiazole-5-carboxylic acid 1.8 g (68%). 1H NMR (300 MHz, DMSO-d6) δ 11.87 (s, 1H).

Workup

  1. customwas consumed
  2. filtrationThe dark suspension was filtered while hot
  3. temperatureThe filtrate was cooled
  4. filtrationThe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-a21b61bc535644b9b17a1f6bd9ccfbba
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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