Lithium Hydroxide → 2-Oxo-4-(trifluoromethyl)-2,3-dihydro-1,3-thiazole-5-carboxylic acid

HRID 2421016Notes

Reaction equation

HRID 2421016 reaction equation
C([N:3]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]([OH:14])=[O:13])[S:5][C:4]1=[O:15])C.[OH-].[Li+]>C1COCC1.O>[O:15]=[C:4]1[NH:3][C:7]([C:8]([F:11])([F:9])[F:10])=[C:6]([C:12]([OH:14])=[O:13])[S:5]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67215248HCID 67215248, compound

Product 1

HCID 198845762-Oxo-4-(trifluoromethyl)-2,3-dihydro-1,3-thiazole-5-carboxylic acidYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2,3-dihydro-2-oxo-4-(trifluoromethyl)-5-thiazolecarboxylic acid (Bionet Research, 2.0 g) in THF (20 mL) was added a solution of lithium hydroxide (0.696 g) in water (20 mL). The mixture was stirred at 50° C. for 72 h, cooled to room temperature and filtered. The filtrate was washed with ethyl acetate (10 mL), acidified to pH 3 using dilute hydrochloric acid and extracted with ethyl acetate (2×25 mL). The combined organic extractions were washed with water (2×50 mL), saturated brine solution, dried (Na2SO4), filtered and concentrated in vacuo to give the subtitle compound as a colourless solid (1.583 g).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with ethyl acetate (10 mL)
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. extractionThe combined organic extractions
  6. washwere washed with water (2×50 mL), saturated brine solution
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87d7de5f0b1b43ca9ff5a55f14fbbd1e
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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