Benzaldehyde → HCID 14459942, compound

HRID 1588753Notes

Reaction equation

HRID 1588753 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][CH:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C[O-].[Na+].Cl>C(O)C.O>[C:19]1(/[CH:18]=[CH:2]/[C:1]([C:4]2[CH:17]=[CH:16][C:7]([CH2:8][CH:9]3[S:13][C:12](=[O:14])[NH:11][C:10]3=[O:15])=[CH:6][CH:5]=2)=[O:3])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 240Benzaldehyde2×HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 14456701HCID 14456701, compound

Product 1

HCID 14459942HCID 14459942, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a slurry of 5-(4-acetylbenzyl)thiazolidine-2,4-dione (4.0 mmol, 1.0 g), and benzaldehyde (4.0 mmol, 0.41 ml) in ethanol (10 ml) was added sodium methoxide (4.8 mmol, 260 mg). The solution was heated to reflux for 1.5 hours, then more benzaldehyde was added and the mixture was heated another 1.5 hours, then cooled, diluted with water (60 ml), acidified with 2N HCl and extracted with ethyl acetate (2×50 ml). The combined extracts were washed with water (50 ml), dried over sodium sulfate and concentrated in vacuo. The residue was recrystallized from isopropanol to give title product as a pale yellow solid (0.33 g, 24%); m.p. 147°-149° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1.5 hours
  3. temperaturethe mixture was heated another 1.5 hours
  4. temperaturecooled
  5. extractionextracted with ethyl acetate (2×50 ml)
  6. washThe combined extracts were washed with water (50 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-b8b1e362d5f64dcfa42e9b6643f58c63
Source dataset
uspto-grants-1993_06
Patent number
US05223522

Reaction notes

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