Diethanolamine → 2-Bis(2-hydroxyethyl)amino-5-nitrobenzonitrile

HRID 1744525

Reaktionsgleichung

Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH:13]([CH2:17][CH2:18][OH:19])[CH2:14][CH2:15][OH:16]>[N+]([O-])([O-])=O.[Ag+]>[OH:16][CH2:15][CH2:14][N:13]([CH2:17][CH2:18][OH:19])[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

2-Chloro-5-nitrobenzonitrile (25.5 g) and silver nitrate (28.5 g) were added to diethanolamine (102 g) and the mixture was stirred at 100° C. for 1 h. The reaction mixture was cooled to room temperature and the solid was filtered off. To the filtrate was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from hydrous methanol to give 2-bis(2-hydroxyethyl)amino-5-nitrobenzonitrile (21.2 g).

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
filtrationthe solid was filtered off
additionTo the filtrate was added water
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customafter which the solvent was evaporated under reduced pressure
additionDiisopropyl ether was added to the residue
customcrystallization
customThe crystals were recrystallized from hydrous methanol

Quellen und Nachweise

ORD-Eintrag: ord-150f4cab4bcf4205af37c08d687579e8
Quelldatensatz: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07015218B1

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