Hydrochloric Acid → 3-Fluoro-4-formylbenzylidene-2,4-thiazolidinedione

HRID 1281148Notes

Reaction equation

HRID 1281148 reaction equation
CO[CH:3]([O:13]C)[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][C:5]=1[F:12].[S:15]1[CH2:19][C:18](=[O:20])[NH:17][C:16]1=[O:21].N1CCCCC1.Cl>C(O)C>[F:12][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[CH:3]=[O:13])[CH:8]=[C:19]1[S:15][C:16](=[O:21])[NH:17][C:18]1=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 184268074-(Dimethoxymethyl)-3-fluorobenzaldehyde

Product 1

HCID 865857473-Fluoro-4-formylbenzylidene-2,4-thiazolidinedioneYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-dimethoxymethyl-3-fluorobenzaldehyde obtained in Example 37 (1.12 g, 5.66 mmol) and 2,4-thiazolidindione (795 mg, 6.79 mmol) in ethanol (20 mL) was added piperidine (0.68 mL, 6.8 mmol), and the mixture was heated to reflux for 13 h. Hydrochloric acid (1 mol/L) was added, and the mixture was extracted with ethyl acetate. The organic layer was combined, washed with brine, dried on anhydrous sodium sulfate, and concentrated under reduced pressure. To the residue were added tetrahydrofuran (25 mL) and hydrchloric acid (1 mol/L; 5 mL), and the mixture was stirred at room temperature for 20 h. Water was added, and the precipitated products were collected by filtration to afford 3-fluoro-4-formylbenzylidene-2,4-thiazolidinedione (696 mg, 49%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 13 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue were added tetrahydrofuran (25 mL) and hydrchloric acid (1 mol/L; 5 mL)
  8. additionWater was added
  9. filtrationthe precipitated products were collected by filtration

Sources & evidence

ORD record
ord-ae7700ed0dbb4276b99217e957dcc98f
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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