5-(4-[2-(N-Benzoyl-N-methylamino)ethoxy]benzylidene)-2,4-thiazolidinedione → 5-(4-[2-(N-Benzoyl-N-methylamino)ethoxy]benzyl)-2,4-thiazolidinedione

HRID 2260717Notes

Reaction equation

HRID 2260717 reaction equation
[C:1]([N:9]([CH2:11][CH2:12][O:13][C:14]1[CH:27]=[CH:26][C:17]([CH:18]=[C:19]2[S:23][C:22](=[O:24])[NH:21][C:20]2=[O:25])=[CH:16][CH:15]=1)[CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.[Pd]>[C:1]([N:9]([CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH:19]2[S:23][C:22](=[O:24])[NH:21][C:20]2=[O:25])=[CH:26][CH:27]=1)[CH3:10])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 545522965-(4-[2-(N-Benzoyl-N-methylamino)ethoxy]benzylidene)-2,4-thiazolidinedione

Product 1

HCID 867491755-(4-[2-(N-Benzoyl-N-methylamino)ethoxy]benzyl)-2,4-thiazolidinedione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

5-(4-[2-(N-Benzoyl-N-methylamino)ethoxy]benzylidene)-2,4-thiazolidinedione (4.01 g) was dissolved in dioxan (400 ml) and hydrogenated at room temperature and pressure in the presence of 10% palladium-charcoal (4 g) for 3.5 hours. A further portion of catalyst (4 g) was added, and the reaction continued for a total of 52 hours. The reaction mixture was filtered through diatomaceous earth, and the solvent evaporated. The resulting gum was recrystallised from dichloromethane-diethyl ether to afford the title compound, mp 139-142° C.

Workup

  1. customcontinued for a total of 52 hours
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. customthe solvent evaporated
  4. customThe resulting gum was recrystallised from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-04bae7ac93414b75904f6aec5fa3b446
Source dataset
uspto-grants-1995_12
Patent number
US05478851

Reaction notes

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