Potassium Hydroxide → 2-Bromoimidazo(4,3-b)(1,3)thiazole-7-carboxylic acid

HRID 1444162Notes

Reaction equation

HRID 1444162 reaction equation
[OH-].[K+].[Br:3][C:4]1[S:8][C:7]2=[C:9]([C:12]([O:14]CC)=[O:13])[N:10]=[CH:11][N:6]2[CH:5]=1>CO>[Br:3][C:4]1[S:8][C:7]2=[C:9]([C:12]([OH:14])=[O:13])[N:10]=[CH:11][N:6]2[CH:5]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59168405Ethyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate

Product 1

HCID 591684042-Bromoimidazo(4,3-b)(1,3)thiazole-7-carboxylic acidYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 M aqueous solution (10 ml) of potassium hydroxide was added to a solution of ethyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate (265 mg, 0.96 mmol) in methanol (20 ml), and the mixture was stirred at room temperature for 18 hr. Methanol was removed by distillation under the reduced pressure, and the reaction solution was poured into 2 M hydrochloric acid (30 ml) under ice cooling to precipitate a solid. The resultant solid was washed with water, and a mixed solvent composed mainly of ethanol and toluene was added thereto. The solvent was removed by distillation under the reduced pressure, and the residue was thoroughly dried to give 2-bromoimidazo[5,1-b]thiazole-7-carboxylic acid (236 mg, quantitative) as a white solid.

Workup

  1. customMethanol was removed by distillation under the reduced pressure
  2. additionthe reaction solution was poured into 2 M hydrochloric acid (30 ml) under ice cooling
  3. customto precipitate a solid
  4. washThe resultant solid was washed with water
  5. additionwas added
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was thoroughly dried

Sources & evidence

ORD record
ord-7bd160cc617245899a1454fe59ccf50e
Source dataset
uspto-grants-2010_02
Patent number
US07662841B2

Reaction notes

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