Sodium Hydroxide → [4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid

HRID 460026Notes

Reaction equation

HRID 460026 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:21])C.[OH-].[Na+]>CO>[CH3:21][C:7]1[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=2)[S:10][C:6]=1[CH2:5][C:4]([OH:22])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17972170Ethyl{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetate2×

Product 1

HCID 17972178[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethyl{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetate (intermediate 13, 0.5 g) in methanol (5 ml) was added 2M sodium hydroxide solution (3 ml). The resulting suspension was stirred at room temperature for 40 minutes, before the solvent was removed in vacuo. The residue was diluted with water (5 ml) acidified (2M hydrochloric acid) and the product extracted twice with ethyl acetate. The combined organic extracts were dried (magnesium sulfate), filtered and evaporated to give the title compound as a yellow solid.

Workup

  1. customwas removed in vacuo
  2. additionThe residue was diluted with water (5 ml)
  3. extractionthe product extracted twice with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ae2ceac6b2e347b3bf9e54495ec1ae92
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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