Potassium Hydroxide → 5-(3-Pyridinylamino)-4-thiazolecarboxylic acid

HRID 2244392Notes

Reaction equation

HRID 2244392 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:5])C.[OH-].[K+]>CO.O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][C:10]2[S:9][CH:8]=[N:7][C:6]=2[C:4]([OH:5])=[O:3])[CH:13]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 64269051HCID 64269051, compound

Product 1

HCID 646318985-(3-Pyridinylamino)-4-thiazolecarboxylic acidYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester (2.90 g, 11.63 mmol) in methanol (24.00 ml) was treated at room temperature with a solution of KOH (1.95 g, 34.90 mmol) in water (18 ml) and stirred at 65° C. for 2 h 45 min. The methanol was evaporated and the residual slurry acidified to pH 5 with 1N HCl. The mixture was sonicated for 15 minutes, then filtered washing with water. The solid was dried under high vacuum overnight, yielding 5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2.37 g, 92%) as a white solid.

Workup

  1. customThe methanol was evaporated
  2. customThe mixture was sonicated for 15 minutes
  3. filtrationfiltered
  4. washwashing with water
  5. customThe solid was dried under high vacuum overnight

Sources & evidence

ORD record
ord-7dc9b42147c94672aba2c8f733672070
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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