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Sodium Hydroxide → 2-Bromothiazole-5-carboxylic acid

HRID 372186
Notes
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Reaction equation

HRID 372186 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:7]([O:9]C)=[O:8])=[CH:5][N:6]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2773502Methyl 2-bromothiazole-5-carboxylate

Product 1

HCID 27632102-Bromothiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture containing 10 g. of 2-bromo-5-methoxycarbonylthiazole, 100 ml. of 10% aqueous sodium hydroxide and 200 ml. of methanol is stirred at 0° C for 5 minutes. The methanol is distilled off in vacuo and the resulting concentrate extracted twice with ethyl acetate. The remaining aqueous phase is acidified by the careful addition of dilute aqueous hydrochloric acid resulting in the formation of a precipitate which is then recovered by filtration and dried under vacuum yielding 2-bromo-5-carboxythiazole.

Workup

  1. additionA mixture containing 10 g
  2. distillationThe methanol is distilled off in vacuo
  3. concentrationthe resulting concentrate
  4. extractionextracted twice with ethyl acetate
  5. additionThe remaining aqueous phase is acidified by the careful addition of dilute aqueous hydrochloric acid resulting in the formation of a precipitate which
  6. filtrationis then recovered by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-88dc2156b4c1436ba9bdcaf5319c1528
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04089865

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes