4,4'-Dimethoxybenzil → 5,6-bis-(4-methoxyphenyl)-1,2,4-triazin-3-thione

HRID 889829Notes

Reaction equation

HRID 889829 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=O)=O)=[CH:5][CH:4]=1.[NH2:21][NH:22][C:23]([NH2:25])=[S:24]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[N:21][NH:22][C:23](=[S:24])[N:25]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 710434,4'-DimethoxybenzilHCID 2723789Thiosemicarbazide

Product 1

HCID 42600365,6-bis-(4-methoxyphenyl)-1,2,4-triazin-3-thioneYield 62.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 4,4′-dimethoxybenzil (13.6 g, 50 mmol) and 6.06 g of thiosemicarbazide (66.5 mmol) in 50 mL of glacial acetic acid were stirred at room temperature then refluxed overnight. The cooled reaction mixture was diluted with 150 mL of water and filtered. The solids were washed with water and dried. The crude product was heated with 55 mL of ethyl acetate, cooled, filtered and dried to give 10.1 g of 5,6-bis-(4-methoxyphenyl)-1,2,4-triazin-3-thione, mp 228–232° C.

Workup

  1. temperaturethen refluxed overnight
  2. customThe cooled reaction mixture
  3. filtrationfiltered
  4. washThe solids were washed with water
  5. customdried
  6. temperatureThe crude product was heated with 55 mL of ethyl acetate
  7. temperaturecooled
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-9bb2a2711b9e4eb3bd3644ac0cfcf6b1
Source dataset
uspto-grants-2006_02
Patent number
US06995157B2

Reaction notes

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