1-Chloro-2,6-dinitrobenzene → 2-((2,6-Dinitrophenyl)amino)benzyl alcohol

HRID 355684

Reaktionsgleichung

Reaktionsgleichung von HRID 355684
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][OH:18]>C(N(CC)CC)C>[N+:11]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][OH:18])([O-:13])=[O:12]

Komponenten

4

Edukt 2

HCID 118141-Chloro-2,6-dinitrobenzeneHCID 214392-Aminobenzyl alcohol

Produkt 1

HCID 540886182-((2,6-Dinitrophenyl)amino)benzyl alcoholAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2.85 g (14 mmol) of 1-chloro-2,6-dinitrobenzene and 1.73 g (14 mmol) of 2-aminobenzyl alcohol were dissolved in 30 ml of triethylamine and heated under reflux for 24 hours. After concentrating, the residue was purified by silica gel column chromatography. Thus 2.2 g of 2-((2,6-dinitrophenyl)amino) benzyl alcohol was obtained. 0.29 g (1 mmol) of this powder was dissolved in 20 ml of dry dimethylformamide. After adding 40 mg (1 mmol) of sodium hydride (in oil, content: 60%), the reaction mixture was stirred at room temperature for 15 minutes and then at 150° C. for 2 hours. After cooling, 200 ml of ethyl acetate was added thereto and the mixture was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography. Thus 0.14 g of the title compound was obtained.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. concentrationAfter concentrating
  4. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d1d738ecaef74f598e25d94a76ef322b
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834462

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