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

HRID 2361857Notes

Reaction equation

HRID 2361857 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-fd766554380c4fd99881dde938436151
Source dataset
uspto-grants-2014_04
Patent number
US08691818B2

Reaction notes

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