3-Methyl-5-[(4-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione → 5-(4-Aminobenzyl)-3-methyl-1,3-thiazolane-2,4-dione

HRID 30645

Reaktionsgleichung

Reaktionsgleichung von HRID 30645
[CH3:1][N:2]1[C:6](=[O:7])[C:5](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[S:4][C:3]1=[O:18]>[C].[Pd].O1CCCC1>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH:5]2[S:4][C:3](=[O:18])[N:2]([CH3:1])[C:6]2=[O:7])=[CH:10][CH:11]=1

Komponenten

4

Edukt 1

HCID 14828843-Methyl-5-[(4-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione

Produkt 1

HCID 27683735-(4-Aminobenzyl)-3-methyl-1,3-thiazolane-2,4-dioneAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3-methyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione (1.0 g), 5% palladium carbon (1.0 g) and tetrahydrofuran (150 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 to give 5-(4-aminobenzyl)-3-methyl-1,3-thiazolidine-2,4-dione as colorless crystals (0.71 g, yield 79%). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 91-92° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-45c08b9c0289483abe2788e113b3c415
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423159B2

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