Ethylenediamine → 2-(4,5-dihydro-1H-imidazol-2-yl)-4,5-dimethoxyaniline

HRID 1787536

Reaktionsgleichung

Reaktionsgleichung von HRID 1787536
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:14](N)[CH2:15][NH2:16]>O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S>[NH:5]1[CH2:14][CH2:15][N:16]=[C:4]1[C:3]1[CH:6]=[C:7]([O:12][CH3:13])[C:8]([O:10][CH3:11])=[CH:9][C:2]=1[NH2:1]

Komponenten

5

Edukt 2

HCID 3301EthylenediamineHCID 7359672-Amino-4,5-dimethoxybenzonitrile

Produkt 1

HCID 575997922-(4,5-dihydro-1H-imidazol-2-yl)-4,5-dimethoxyanilineAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14817Phosphorus sulfide (P2S5)KatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

2-Amino-4,5-dimethoxybenzonitrile (5.0 g, 28 mmol) was added to ethylenediamine (7.9 g, 131 mmol) at room temperature. The resulting solution was warmed to 40, and a catalitic amount of diphosphorus pentasulfide (50 mg) was added. The mixture was heated to 80-90, and the stirring was continued overnight. The reaction mixture was diluted with water, and the resulting precipitate was collected by filtration to give 2-(4,5-dihydro-1H-imidazol-2-yl)-4,5-dimethoxyaniline (5.1 g, 82%) as a solid.

Aufarbeitung

  1. temperatureThe resulting solution was warmed to 40
  2. temperatureThe mixture was heated to 80-90
  3. filtrationthe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-2bb011c602b84852991db2f701478f2d
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511041B2

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