4-Hydroxybenzaldehyde → (5E)-5-[(4-Hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione

HRID 1157985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157985
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[S:10]1[CH2:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].N1CCCCC1.CO>C(O)(=O)C.O>[CH:4]1[C:5](/[CH:6]=[C:14]2\[C:13]([NH:12][C:11]([S:10]\2)=[O:16])=[O:15])=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=1

Komponenten

7

Edukt 4

HCID 1264-Hydroxybenzaldehyde2×HCID 887MethanolHCID 5437Thiazolidinedione2×HCID 8082Piperidine

Produkt 1

HCID 1276528(5E)-5-[(4-Hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy benzaldehyde, 36 (3 g, 24.6 mmol), 2,4-thiazolidinedione, 37 (2.9 g, 24.8 mmol), piperidine (2.5 mL) and methanol (100 mL) was refluxed for 18 h. The reaction mixture was poured into water and acidified with acetic acid to give 38, which was recrystallised from methanol. Yield 4.7 g (86%); mp 296-298° C.; MS (FAB) 222 (M++1); IR (KBr) 3404, 3123, 1723, 1678; 1H NMR (200 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.46 (d, J=8.6 Hz, 2H), 6.93 (d, J=8.6 Hz, 2H).

Aufarbeitung

  1. temperaturewas refluxed for 18 h

Quellen und Nachweise

ORD-Eintrag
ord-86bd44a3b7fc4e1399930d3d4ee1ebad
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807712B2

Notizen zur Reaktion

Wird geladen…