1,2-Bis(4-methylphenyl)-1,2-ethanedione → 3-Amino-5,6-bis(4-methylphenyl)-1,2,4-triazine

HRID 1484494Notes

Reaction equation

HRID 1484494 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=O)=O)=[CH:4][CH:3]=1.S(O)(=O)(=O)C.S(O)(=O)(=O)C.[NH2:29][NH:30][C:31]([NH2:33])=[NH:32]>C(O)C>[NH2:33][C:31]1[N:30]=[N:29][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:32]=1

Participants

4

Reactant 2

HCID 769961,2-Bis(4-methylphenyl)-1,2-ethanedioneHCID 178505340HCID 178505340, compound

Product 1

HCID 581031023-Amino-5,6-bis(4-methylphenyl)-1,2,4-triazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 4,4′-dimethylbenzil (2.38 g; 0.01 mol), aminoguanidine bismesylate (3.33 g; 0.0125 mol) and ethanol (10 cm3) was heated under reflux until no starting material remained (4 hrs) when a cream solid was deposited. The mixture was evaporated to half volume and basified with 880 ammonia+water (1:1; 4 cm3). On standing, bight yellow prisms were deposited. The product was filtered off, washed with ethanol+water (1:1) and dried in vacuo at 450.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux until no starting material
  3. custom(4 hrs) when
  4. customThe mixture was evaporated to half volume and basified with 880 ammonia+water (1:1; 4 cm3)
  5. filtrationThe product was filtered off
  6. washwashed with ethanol+water (1:1)
  7. customdried in vacuo at 450

Sources & evidence

ORD record
ord-aaec2d26c4874314b39934bd1d885e46
Source dataset
uspto-grants-2016_08
Patent number
US09422253B2

Reaction notes

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