Lithium Hydroxide → 2-(Pyridin-2-yl)-1,3-thiazole-5-carboxylic acid

HRID 1260322Notes

Reaction equation

HRID 1260322 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:7][CH:6]=1)=[O:4].[OH-].[Li+].ClCCl>C1COCC1.CO>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 57688443Methyl 2-(pyridin-2-yl)thiazole-5-carboxylate

Product 1

HCID 232838552-(Pyridin-2-yl)-1,3-thiazole-5-carboxylic acidYield 93.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Pyridin-2-yl-thiazol-5-carboxylic acid methyl ester (0.34 g, 1.55 mmol) was dissolved in a THF/methanol (5 ml/1 ml) mixture, cooled to 0° C. and treated with lithium hydroxide (4.7 ml, 1N aqueous solution). The reaction mixture was allowed to warm-up to ambient temperature, stirred at that temperature for 30 min and the pH value was subsequently adjusted to ˜5. The resulting suspension was treated with dichloromethane (50 ml) and filtered. The precipitate was washed with water and dichloromethane, the filtrate was extracted with dichloromethane. The combined organic phases were dried, evaporated and combined with the precipitate to yield the product as light brown solid (0.3 g, 92%). MS: M=161.1 (M-CO2—H)−

Workup

  1. temperatureto warm-up to ambient temperature
  2. filtrationfiltered
  3. washThe precipitate was washed with water and dichloromethane
  4. extractionthe filtrate was extracted with dichloromethane
  5. customThe combined organic phases were dried
  6. customevaporated

Sources & evidence

ORD record
ord-2b032ecaf5f24dff94b6e06c1c1b144d
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

Loading…