1,3-Dibromopropane → HCID 20427608, Verbindung

HRID 615316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 615316
[CH2:1]([S:3][C:4]1[NH:5][C:6](=[O:23])[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]=1[C:9]#[N:10])[CH3:2].[H-].[Na+].[Br:26][CH2:27][CH2:28][CH2:29]Br>O1CCOCC1>[Br:26][CH2:27][CH2:28][CH2:29][N:5]1[C:6](=[O:23])[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([C:9]#[N:10])=[C:4]1[S:3][CH2:1][CH3:2]

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 132361792-(Ethylsulfanyl)-5-oxo-4,4-diphenyl-4,5-dihydro-1H-pyrrole-3-carbonitrile

Produkt 1

HCID 20427608HCID 20427608, VerbindungAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

One dissolves 15.0 g 2-ethylthio-5-oxo-4,4-diphenyl-2-pyrroline-3-carbonitrile in 500 ml abs. dioxan, adds 1.4 g sodium hydride (80%) in white oil) thereto and boils under reflux for one hour. One allows to cool somewhat, adds 100.0 g 1,3-dibromopropane thereto and further boils for 48 hours. Thereafter, the reaction mixture is filtered, the solvent and the excess dibromopropane are distilled off under water pump vacuum and the residue is triturated with diisopropyl ether. One obtains 14.0 g 1-(3-bromopropyl)-2-ethylthio-5-oxo-4,4-diphenyl-2-pyrroline-3-carbonitrile of mp 97° C.

Aufarbeitung

  1. temperatureunder reflux for one hour
  2. temperatureto cool somewhat
  3. filtrationThereafter, the reaction mixture is filtered
  4. distillationthe solvent and the excess dibromopropane are distilled off under water pump vacuum
  5. customthe residue is triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-846fb5838c8b48beb819b2e17b18e5c6
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04499089

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