Hydrochloric Acid → HCID 178426865, compound

HRID 1281154Notes

Reaction equation

HRID 1281154 reaction equation
CO[CH:3]([O:14]C)[C:4]1[CH:5]=[C:6]([CH3:13])[C:7]([CH:11]=O)=[N:8][C:9]=1[CH3:10].[S:16]1C[C:19](=[O:21])[NH:18][C:17]1=[O:22].N1CCCCC1.Cl>C(O)C.O>[CH:3]([C:4]1[CH:5]=[C:6]([CH3:13])[C:7](=[C:11]2[S:16][C:17](=[O:22])[NH:18][C:19]2=[O:21])[NH:8][C:9]=1[CH3:10])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 18426857HCID 18426857, compound

Product 1

HCID 178426865HCID 178426865, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 5-dimethoxymetyl-3,6-dimethyl-2-pyridinecarboxaldehyde (53 mg, 0.25 mmol) and 2,4-thiazolidindione (44 mg, 0.38 mmol) in ethanol (5 mL) was added piperidine (0.038 mL, 0.38 mmol), and the mixture was heated to reflux for 16 h. Hydrochloric acid (1 mol/L; 0.4 mL) and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried on anhydrous sodium sulfate, and concentrated under reduced pressure. To the residue were added tetrahydrofuran (4 mL) and hydrochloric acid (1 mol/L; 0.5 mL), and the mixture was stirred at room temperature for 7 h. Water was added, and the precipitated products were collected by filtration to afford 5-formyl-3,6-dimethylpyridin-2-ylidene-2,4-thiazolidinedione (43 mg, 66%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue were added tetrahydrofuran (4 mL) and hydrochloric acid (1 mol/L; 0.5 mL)
  8. additionWater was added
  9. filtrationthe precipitated products were collected by filtration

Sources & evidence

ORD record
ord-99ab4a90bdae47ac92abde4480ad17d0
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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