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

HRID 555959

Reaction equation

HRID 555959 reaction equation
[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

Participants

4

Reactant 2

HCID 2146AminoguanidineHCID 710434,4'-Dimethoxybenzil

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-5dcf1171b2f548c0a44a471a443cfc23
Source dataset
uspto-grants-2011_11
Patent number
US08053573B2

Linked notes

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