StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Water → 5-(2-Thienylmethylene)-3-[4-(imidazo[1,2-a]pyridin-5-ylthio) butyl]thiazolidine-2,4-dione

HRID 357030
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 357030
Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=[C:22]1[S:26][C:25](=[O:27])[NH:24][C:23]1=[O:28].O>CN(C)C=O>[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=[C:22]1[S:26][C:25](=[O:27])[N:24]([CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)[C:23]1=[O:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 36416932,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-HCID 18936641Imidazo[1,2-a]pyridine,5-[(4-chlorobutyl)thio]-

Produkt 1

HCID 572278865-(2-Thienylmethylene)-3-[4-(imidazo[1,2-a]pyridin-5-ylthio) butyl]thiazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent, hexane/ethyl acetate=2/1→1/1→ethyl acetate)
  7. customThe resulting crude crystal was purified by recrystallization (solvent, chloroform/diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-62d37ea2ee774ab8a631b79813a27a4e
Quelldatensatz
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05840732

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion