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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 84556Erstellt: 24. Oktober 2026

Toluene → 3-(9-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulen-2-yl)-4-(2-chloro-4-fluoro-phenyl)-4H-[1,2,4]triazole

https://huagongshe.com/de/reaction/84556

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTolueneHCID 1140—
EduktTrifluoroacetic acidHCID 6422—
EduktBenzenamine, 2-chloro-4-fluoro-HCID 75013—
Edukt2-(9-Bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulen-2-yl)-[1,3,4]oxadiazoleHCID 66886809—
LösungsmittelEthyl AcetateHCID 8857—
Produkt3-(9-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulen-2-yl)-4-(2-chloro-4-fluoro-phenyl)-4H-[1,2,4]triazoleHCID 5790042268%

Reaktionsbedingungen

Temperatur160 °C

Reaktionsschritte

A microwave tube was charged with 2-(9-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulen-2-yl)-[1,3,4]oxadiazole (0.64 g; 1.83 mmol), 2-chloro-4-fluoroaniline (0.44 ml; 3.68 mmol), TFA (0.27 ml; 3.63 mmol) and toluene (5 ml). The mixture was heated in a microwave at 160° C. for 30 min., diluted with EtOAc (150 ml) and washed with satd. NaHCO3. The organic layer was dried (MgSO4), concentrated and purified by ISCO to give 267 as a cream-coloured solid (0.59 g; 68%). δH (400 MHz, CDCl3) 3.14 (t, J=5.2, 2H), 4.29 (t, J=5.2, 2H), 6.91 (d, J=8.4, 1H), 6.93 (s, 1H), 7.22-7.27 (m, 2H), 7.43-7.51 (m, 2H), 7.65 (d, J=2.4, 1H), 8.22 (s, 1H). [M+H]+: 478

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08846762B2
Quelldatensatzuspto-grants-2014_09
ORD IDord-7cc49108f3ac4bd3b30d40504cab7c2d
Quellennotizuspto-grants-2014_09