2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68961219, compound

HRID 1726923Notes

Reaction equation

HRID 1726923 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][N:4]1[C:9](=[O:10])[CH2:8][NH:7][C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5]1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(OCC)(=O)C>[F:18][C:2]([F:1])([F:17])[CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[N:7][C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178516750HCID 178516750, compound

Product 1

HCID 68961219HCID 68961219, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.51 g of 1-(2,2,2-trifluoroethyl)-3-phenyl-4,5-dihydro-1,2,4-triazin-6-one (2.0 mmol) and 0.48 g of DDQ (2.1 mmol) in 20 mL of ethyl acetate was stirred at room temperature overnight, then heated to 70° C. for 2 hours. The reaction mixture was cooled and washed with aqueous potassium carbonate, water (2 times) and brine, dried over magnesium sulfate, filtered and stripped. The product was dissolved in ethyl acetate/methylene chloride and treated with silica gel, then filtered through silica gel over Celite to give 0.40 g of 1-(2,2,2-trifluoroethyl)-3-phenyl-1,2,4-triazin-6-one, melting point 129-131° C.

Workup

  1. temperatureheated to 70° C. for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. washwashed with aqueous potassium carbonate, water (2 times) and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. dissolutionThe product was dissolved in ethyl acetate/methylene chloride
  7. additiontreated with silica gel
  8. filtrationfiltered through silica gel over Celite

Sources & evidence

ORD record
ord-e4c987bfb9dc48828762fc9f289ab8b8
Source dataset
uspto-grants-2009_02
Patent number
US07494996B2

Reaction notes

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