2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-Phenyl-1,2,4-triazin-6(1H)-one

HRID 1902179Notes

Reaction equation

HRID 1902179 reaction equation
[C:1]1([C:7]2[NH:12][CH2:11][C:10](=[O:13])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(OCC)(=O)C>[C:1]1([C:7]2[N:12]=[CH:11][C:10](=[O:13])[NH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178516749HCID 178516749, compound

Product 1

HCID 205157783-Phenyl-1,2,4-triazin-6(1H)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To 0.60 g. 3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one dissolved in 40 ml ethyl acetate was added 0.80 g. DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone). The solution immediately became green and was stirred at about 25° C. for 16 hours. The reaction mixture was then refluxed for 3 hours and cooled in an ice bath. The solid was collected and washed with three 50 ml portions of hexane. Yield 0.37 g. 64% Yield.

Workup

  1. additionwas added 0.80 g
  2. temperatureThe reaction mixture was then refluxed for 3 hours
  3. temperaturecooled in an ice bath
  4. customThe solid was collected
  5. washwashed with three 50 ml portions of hexane

Sources & evidence

ORD record
ord-2462e0a915284081b4457b5e63127c35
Source dataset
uspto-grants-1982_12
Patent number
US04362550

Reaction notes

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