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Hydrochloric Acid → 5-Methyl-1,3-thiazole-4-carboxylic acid

HRID 1667856
Notes
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Reaction equation

HRID 1667856 reaction equation
[CH3:1][C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([OH:9])=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 37818647Methyl 5-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 141093205-Methyl-1,3-thiazole-4-carboxylic acidYield 50.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-methyl-1,3-thiazole-4-carboxylate (1.17 g, 7.4 mmol) in methanol (15 mL) was added 8N aqueous sodium hydroxide solution (2.00 mL), and the mixture was stirred at room temperature for 18 hr. 6N Hydrochloric acid (2.67 mL) was added to the mixture, and the mixture was concentrated under reduced pressure. Water was added to the residue, and the precipitate was collected by filtration, and washed with water. The precipitate was suspended in a mixed solvent of ethyl acetate (9 mL) and ethanol (1 mL), and the mixture was stirred at 80° C. for 3 min. After allowing to cool to room temperature, the precipitate was collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give the title compound (531 mg, yield 50%) as a pale-yellow solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. stirringthe mixture was stirred at 80° C. for 3 min
  6. temperatureto cool to room temperature
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with ethyl acetate
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-0cf7137af4c6440eaef37b7eccb486bf
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044049B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes