Benzaldehyde → 5-Benzyl-1,3-thiazolidine-2,4-dione

HRID 2260701Notes

Reaction equation

HRID 2260701 reaction equation
C(=O)C1C=CC=CC=1.S1CC(=O)NC1=O.[CH:16](=[C:23]1[S:27][C:26](=[O:28])[NH:25][C:24]1=[O:29])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCOCC1.[Pd]>[CH2:16]([CH:23]1[S:27][C:26](=[O:28])[NH:25][C:24]1=[O:29])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5437ThiazolidinedioneHCID 1991545-Benzylidene-2,4-thiazolidinedione

Product 1

HCID 31570135-Benzyl-1,3-thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Benzaldehyde (10.6 g) and 2,4-thiazolidinedione (11.7 g) were reacted together by a procedure analogous to that described in Example 1. The resulting material, 5-benzylidene-2,4-thiazolidinedione (18.5 g) was dissolved in dioxan (300 ml) and hydrogenated over 10% Palladium-charcoal (18.5 g) at 200 psi, overnight. The mixture was filtered through diatomaceous earth, the filter cake thoroughly washed with dioxan, and the combined dioxan solutions evaporated to afford the title compound, mp 83°-86° C.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter cake thoroughly washed with dioxan
  3. customthe combined dioxan solutions evaporated

Sources & evidence

ORD record
ord-ae1aed16bebd4500981826bbe449e6f2
Source dataset
uspto-grants-1995_12
Patent number
US05478850

Reaction notes

Loading…