Benzyl Bromide → 1-Benzyl-2-[4-(diethylamino)styryl]pyridinium bromide

HRID 365126

Reaktionsgleichung

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].[CH2:8]([Br:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:16]([N:18]([CH2:27][CH3:28])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[CH3:17].N1CCCCC1>C(O)(C)C.CO>[Br-:15].[CH2:8]([N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:23][C:22]1[CH:25]=[CH:26][C:19]([N:18]([CH2:16][CH3:17])[CH2:27][CH3:28])=[CH:20][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

2-Picoline (9.3 g, 0.1 mole) and benzyl bromide (17.1 g, 0.1 mole) were refluxed in isopropanol (50 ml) overnight. The solvent was evaporated giving an oil which was heated at 100° C. for six hours. The resulting crude oil (8.5 g, 0.032 mole) and 4-diethylaminobenzaldehyde (6.0 g, 0.033 mole) were refluxed in methanol (40 ml) in the presence of piperidine (0.2 ml) under nitrogen for three hours. On cooling dark-coloured crystals were obtained which were collected to give 1-benzyl-2-[4-(diethylamino)styryl]pyridinium bromide (6.2 g), melting point 231°-233° C.

Aufarbeitung

customThe solvent was evaporated
customgiving an oil which
temperatureOn cooling dark-coloured crystals
customwere obtained which
customwere collected

Quellen und Nachweise

ORD-Eintrag: ord-d040665acb754439b3780d1ccacf8331
Quelldatensatz: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04608379

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