Sodium hydride → N-(4,5-dimethoxy-2-nitrophenyl)-N',N'-dimethylethylenediamine

HRID 373064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373064
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.Cl.Cl[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20].[H-].[Na+]>CN(C)C=O.[OH-].[Na+]>[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH:7][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 46531524,5-Dimethoxy-2-nitroanilineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Produkt 1

HCID 19811371N-(4,5-dimethoxy-2-nitrophenyl)-N',N'-dimethylethylenediamineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4,5-dimethoxy-2-nitroaniline (0.81 g) and 2-chloroethyldimethylamine hydrochloride (0.73 g) in N,N-dimethylformamide (20 ml) was added sodium hydride (0.36 g) in small portions with ice-cooling and the reaction mixture was heated at 60° C. for 2 hours. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was successively washed with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent:chloroform:methanol=15:1) to give 0.77 g of N-(4,5-dimethoxy-2-nitrophenyl)-N',N'-dimethylethylenediamine.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography (eluent:chloroform:methanol=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-347687bd589543e98b1cb60f2ce4f893
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162318

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