4-(4-Oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzoic acid → 3-(4-Carboxyphenyl)-5-(4-beta-D-galactopyranosyloxy-3-methoxyphenylmethylene)-2-thioxothiazolidin-4-one

HRID 1588197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588197
[O:1]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:14]=1[O:21][CH3:22])[C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[K].[C:24]([C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:37](=[O:38])[CH2:36][S:35][C:34]2=[S:39])=[CH:29][CH:28]=1)([OH:26])=[O:25]>C(O)C.N1CCCCC1>[C:24]([C:27]1[CH:28]=[CH:29][C:30]([N:33]2[C:37](=[O:38])[C:36](=[CH:19][C:16]3[CH:17]=[CH:18][C:13]([O:1][C@@H:2]4[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]4[OH:4])=[C:14]([O:21][CH3:22])[CH:15]=3)[S:35][C:34]2=[S:39])=[CH:31][CH:32]=1)([OH:26])=[O:25]

Komponenten

6

Edukt 3

HCID 2335384-(4-Oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzoic acidHCID 5462222PotassiumHCID 115151674-O-(alpha-d-galactopyranosyl)vanillin

Produkt 1

HCID 542635073-(4-Carboxyphenyl)-5-(4-beta-D-galactopyranosyloxy-3-methoxyphenylmethylene)-2-thioxothiazolidin-4-oneAusbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred suspension of 4-formyl-2-=methoxyphenyl β-D-galactopyranoside (1c)(0.47 g, 1.5 mmol) in absolute ethanol (25 ml) containing piperidine (1 drop), was added the potassium salt of 3-(4-carboxyphenyl)-2-thioxothiazolidin-4-one (0.44 g, 1.5 mmol) and the suspension was heated under gentle reflux for 2 h. A yellow solid separated which was filtered hot and washed with small portions of boiling methanol and ethyl acetate followed by ether to give the product (0.2 g, 22%) as the potassium salt, m.p. decomp.>230° C.

Aufarbeitung

  1. temperaturethe suspension was heated
  2. temperatureunder gentle reflux for 2 h
  3. customA yellow solid separated which
  4. filtrationwas filtered hot
  5. washwashed with small portions of boiling methanol and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fd433d386cac478a96b23796dfd294d8
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05221606

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