3-Ethyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione → HCID 85969147, compound

HRID 30646Notes

Reaction equation

HRID 30646 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[C:6](=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[S:5][C:4]1=[O:19])[CH3:2]>[C].[Pd].O1CCCC1>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH:6]2[S:5][C:4](=[O:19])[N:3]([CH2:1][CH3:2])[C:7]2=[O:8])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 47605383-Ethyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione

Product 1

HCID 85969147HCID 85969147, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-ethyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione (3.60 g), 5% palladium carbon (5.0 g) and tetrahydrofuran (300 mL) was subjected to catalytic reduction under hydrogen pressure of 5.0 kgf·cm−2. The catalyst was removed by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and 5-(4-aminobenzyl)-3-ethyl-1,3-thiazolidine-2,4-dione was obtained as yellow crystals (3.05 g, yield 94%) from a fraction eluted with hexane-ethyl acetate (3:1-1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave yellow prism crystals. melting point: 103-104° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1d2d9bda4db54d6ca15f1aa046b8964d
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

Loading…