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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 357030Erstellt: 24. Oktober 2026

Water → HCID 57227886, Verbindung

https://huagongshe.com/de/reaction/357030

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktWaterHCID 962—
Edukt2,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-HCID 3641693—
EduktImidazo[1,2-a]pyridine,5-[(4-chlorobutyl)thio]-HCID 18936641—
LösungsmittelDimethylformamideHCID 6228—
ProduktHCID 57227886HCID 57227886—

Reaktionsbedingungen

Temperatur80 °C

Reaktionsschritte

To a solution of 1.81 g (7.5 mmol) of 5-(4-chlorobutylthio)imidazo[1,2-a]pyridine and 1.59 g (7.5 mmol) of 5-(2-thienylmethylene)thiazolidine-2,4-dione in 70 ml of N,N-dimethylformamide, 1.12 ml (7.5 mmol) of 1,8-diazabicyclo[5.4.0-7-undecene was added, followed by heating at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, hexane/ethyl acetate=2/1→1/1→ethyl acetate). The resulting crude crystal was purified by recrystallization (solvent, chloroform/diethyl ether) to yield 1.54 g (49.5%, light yellow crystal) of the desired product.m.p. 116.0°-117.0° C.; 1H-NMR (CDCl3, 200 MHz) δ 1.64-1.92 (4H, m), 3.03 (2H, t, J=7.0 Hz), 3.76 (2H, t, J=7.0 Hz), 6.92 (1H, dd, J=1.0, 7.0 Hz), 7.15 (1H, dd, J=7.2, 9.2 Hz), 7.21 (1H, dd, J=3.8, 5.2 Hz), 7.42 (1H, d, J=3.6 Hz), 7.58 (1H, d, J=9.0 Hz), 7.68 (1H, d, J=5.0 Hz), 7.70 (1H, d, J=1.4 Hz), 7.85 (1H, s), 8.05 (1H, s); IR (KBr) 1728, 1678, 1599, 1369, 1128, 773, 727 cm-1 ; Anal. Calcd for C19H17N3O2S3 : C, 54.92; H, 4.12; N, 10.11. Found: C, 54.67, H, 4.18; N, 10.03

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05840732
Quelldatensatzuspto-grants-1998_11
ORD IDord-62d37ea2ee774ab8a631b79813a27a4e
Quellennotizuspto-grants-1998_11