Ethanol → 4-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid

HRID 925272Notes

Reaction equation

HRID 925272 reaction equation
C[O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[S:10][CH2:11][CH2:12][C:13]([F:22])([F:21])[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:4].[OH-].[K+].CCO>CCO.O>[F:22][C:13]([F:21])([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:12][CH2:11][S:10][C:6]1[N:7]=[CH:8][S:9][C:5]=1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 867201694-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 867201704-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acidYield 83%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
120 °C

Procedure

4-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid methyl ester (0.88 g, 2.54 mmol) is taken in EtOH/water (1:1) (4 ml) powdered KOH (0.36 g, 6.34 mmol) is added. The mixture is refluxed vigorously at 120° C. for 16 h. After completion of the reaction, EtOH is evaporated. The residue is diluted with water (20 ml), acidified with 2M hydrochloric acid to pH 3, and extracted with EtOAc (3×30 ml). The combined organic layers are dried over sodium sulfate, evaporated to dryness yielding 4-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid (0.7 g, 2.09 mmol, 83%).

Workup

  1. additionis added
  2. customis evaporated
  3. additionThe residue is diluted with water (20 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1bc70a2ad4a64144987387616d326357
Source dataset
uspto-grants-2016_03
Patent number
US09284286B2

Reaction notes

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