Lithium hydroxide, monohydrate → 2-(6-Chloropyridin-3-yl)-4-methyl-1,3-thiazole-5-carboxylic acid

HRID 1710788Notes

Reaction equation

HRID 1710788 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([O:16]CC)=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([OH:16])=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59457501Ethyl 2-(6-chloropyridin-3-yl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 594575142-(6-Chloropyridin-3-yl)-4-methyl-1,3-thiazole-5-carboxylic acidYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of ethyl 2-(6-chloropyridin-3-yl)-4-methyl-1,3-thiazole-5-carboxylate i97 (0.55 g, 1 eq, 1.94 mmol) and lithium hydroxide monohydrate (0.16 g, 2 eq, 3.89 mmol) in tetrahydrofurane/water (28 ml 1:0.1, v/v) is stirred at room temperature for 1 h 30. The mixture is diluted with water and extracted with ethyl acetate. The aqueous layer is then acidified to pH 2 with 2 N hydrochloric acid. The precipitate that forms is filtered and washed with water to give 0.48 g of 2-(6-chloropyridin-3-yl)-4-methyl-1,3-thiazole-5-carboxylic acid i98.

Workup

  1. extractionextracted with ethyl acetate
  2. filtrationThe precipitate that forms is filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-563a84e3810b4db08470851a487d37dd
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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