Isopropanol → Bis(3-diethylaminopropyl) 9-ethylcarbazole-3,6-dicarboxylate dihydrochloride

HRID 1580164

Reaktionsgleichung

Reaktionsgleichung von HRID 1580164
[CH:1](O)([CH3:3])[CH3:2].[CH2:5]([N:7]1[C:19]2[CH:18]=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([C:23]([OH:25])=[O:24])[CH:12]=2)[CH3:6].[CH2:26]([N:28]([CH2:33][CH3:34])[CH2:29][CH2:30][CH2:31][Cl:32])[CH3:27]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CCOCC>[ClH:32].[ClH:32].[CH2:5]([N:7]1[C:19]2[CH:18]=[CH:17][C:16]([C:20]([O:22][CH2:2][CH2:1][CH2:3][N:7]([CH2:8][CH3:9])[CH2:5][CH3:6])=[O:21])=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([C:23]([O:25][CH2:31][CH2:30][CH2:29][N:28]([CH2:33][CH3:34])[CH2:26][CH3:27])=[O:24])[CH:12]=2)[CH3:6]

Komponenten

6

Edukt 3

HCID 3776IsopropanolHCID 669183-Chloropropyl(diethyl)amineHCID 37979149-ethyl-9H-carbazole-3,6-dicarboxylic acid

Produkt 1

HCID 12331707Bis(3-diethylaminopropyl) 9-ethylcarbazole-3,6-dicarboxylate dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To 250 ml. of isopropanol was added 10.0 g. (0.035 mole) of 9-ethylcarbazole-3,6-dicarboxylic acid, 21.2 g. (0.14 mole) of 3-diethylaminopropylchloride and 0.5 ml. of 60% aqueous benzyltrimethylammonium chloride. The solution was heated at reflux for 2 hours with stirring and then allowed to stir overnight at room temperature. Addition of ether to the reaction mixture gave the crystalline product which was recrystallized twice from methanol-acetone, m.p. 233°-234°, λmaxEtOH 252, E1 cm1% 865.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 hours
  3. stirringto stir overnight at room temperature
  4. customgave the crystalline product which
  5. customwas recrystallized twice from methanol-acetone, m.p. 233°-234°, λmaxEtOH 252, E1 cm1% 865

Quellen und Nachweise

ORD-Eintrag
ord-9ac0d308e32140a2ab9deff1902bcb74
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03932456

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