Aminoguanidine → 5,6-Bis-(4-methoxy-phenyl)-[1,2,4]triazin-3-ylamine

HRID 555959

Reaktionsgleichung

Reaktionsgleichung von HRID 555959
[C:1]([NH2:5])([NH2:4])=[N:2][NH2:3].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=O)=[CH:10][CH:9]=1>C(O)C>[NH2:4][C:1]1[N:2]=[N:3][C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[C:14]([C:11]2[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=2)[N:5]=1

Komponenten

4

Edukt 2

HCID 2146AminoguanidineHCID 710434,4'-Dimethoxybenzil

Produkt 1

HCID 598591245,6-Bis-(4-methoxy-phenyl)-[1,2,4]triazin-3-ylamineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Aminoguanidine (2.450 g, 2.21 mmol) is added to a solution of 1,2-bis(4-methoxyphenyl)-ethane-1,2-dione prepared according to example 1 (5 g, 18.5 mmol) in ethanol (50 ml). The mixture is heated at reflux for 12 hours. After returning to ambient temperature, the precipitate obtained is filtered, washed with ethanol and is dried to yield a yellow solid. The residue is purified by chromatography on a silica gel (dichloromethane/triethylamine 0.5%) to yield 3.7 g (65%) of a yellow solid. δH (200 MHz, CDCl3), 3.88 (s; 6H), 5.51 (s; 2H), 6.92 (m; 4H), 7.41 (m; 4H).

Aufarbeitung

  1. customprepared
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 12 hours
  4. customAfter returning to ambient temperature
  5. customthe precipitate obtained
  6. filtrationis filtered
  7. washwashed with ethanol
  8. customis dried
  9. customto yield a yellow solid
  10. customThe residue is purified by chromatography on a silica gel (dichloromethane/triethylamine 0.5%)

Quellen und Nachweise

ORD-Eintrag
ord-5dcf1171b2f548c0a44a471a443cfc23
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053573B2

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