Acetic Acid → 4-Methyl-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

HRID 1679369Notes

Reaction equation

HRID 1679369 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[N:5]=[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[S:7][C:8]=1[C:9]([O:11]CC)=[O:10].Cl.C(O)(=O)C>O.C(O)C>[CH3:3][C:4]1[N:5]=[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[S:7][C:8]=1[C:9]([OH:11])=[O:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 619088Ethyl 4-methyl-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 27634894-Methyl-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (22 g., 0.55 mole) in water (300 ml.) was mixed with a solution of ethyl 4-methyl-2-(3-pyridyl)-5-thiazolecarboxylate (124 g., 0.50 mole) in 95% ethanol (150 ml.). The mixture was heated and stirred for about ten minutes on a steam bath, and then allowed to stand for one hour without further heating. When the ice-cooled reaction mixture was neutralized with dilute hydrochloric acid and acidified with acetic acid, a thick precipitate of finely divided white solid was obtained. The solid was collected by filtration, washed thoroughly with water, and dried in an oven at 110° C. The product (106 g., 96% yield) melted with decomposition at 249°-250° C.

Workup

  1. temperatureThe mixture was heated
  2. customreaction mixture
  3. customa thick precipitate of finely divided white solid was obtained
  4. filtrationThe solid was collected by filtration
  5. washwashed thoroughly with water
  6. customdried in an oven at 110° C
  7. custommelted with decomposition at 249°-250° C.

Sources & evidence

ORD record
ord-8c195d3f6b494aabbe63bc98f79bf1d7
Source dataset
uspto-grants-1978_03
Patent number
US04080457

Reaction notes

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