HCID 53964150, compound → HCID 86749174, compound

HRID 2260702Notes

Reaction equation

HRID 2260702 reaction equation
[C:1]1(=[O:28])[N:5]([CH2:6][CH2:7][O:8][C:9]2[CH:22]=[CH:21][C:12]([CH:13]=[C:14]3[S:18][C:17](=[O:19])[NH:16][C:15]3=[O:20])=[CH:11][CH:10]=2)[C:4](=[O:23])[C:3]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:2]12>O1CCOCC1.[Pd]>[C:4]1(=[O:23])[N:5]([CH2:6][CH2:7][O:8][C:9]2[CH:22]=[CH:21][C:12]([CH2:13][CH:14]3[S:18][C:17](=[O:19])[NH:16][C:15]3=[O:20])=[CH:11][CH:10]=2)[C:1](=[O:28])[C:2]2=[CH:27][CH:26]=[CH:25][CH:24]=[C:3]12

Participants

4

Reactant 1

HCID 53964150HCID 53964150, compound

Product 1

HCID 86749174HCID 86749174, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 5-(4-(2-phthalimidoethoxy)benzylidene)-2,4-thiazolidinedione (3.25 g) in dioxan (100 ml)was hydrogenated at room temperature and pressure in the presence of 10% palladium-charcoal (5 g) for 18 hours. A further portion of catalyst (5 g) was added, and the reaction continued for a total of 23 hours. The reaction mixture was filtered through diatomaceous earth, and the solvent evaporated. The resulting gum was crystallised from methanol-dioxan to afford the title compound, mp 192°-4° C.

Workup

  1. customwas hydrogenated at room temperature
  2. customcontinued for a total of 23 hours
  3. filtrationThe reaction mixture was filtered through diatomaceous earth
  4. customthe solvent evaporated
  5. customThe resulting gum was crystallised from methanol-dioxan

Sources & evidence

ORD record
ord-a7994593be7b4535b2289fb0dcee9833
Source dataset
uspto-grants-1995_12
Patent number
US05478850

Reaction notes

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