2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178461867, compound

HRID 394477Notes

Reaction equation

HRID 394477 reaction equation
[C:1]1([CH:7]([NH:9][C:10]2[N:15]=[C:14]([C@H:16]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)=[N:20][NH:19][C:18](=[O:32])[CH2:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(#N)C>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[C:18]([OH:32])[N:19]=[N:20][C:21]=3[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:31])[F:30])[CH:23]=3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[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 70023896(s)-5-[2-(1-Phenylethylamino)pyrimidin-4-yl]-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 178461867HCID 178461867, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 8 (4.24 g, 9.66 mmol), 2,3-dichloro-5,6-dicyano-4-benzoquinone (4.38 g, 19.3 mmol), and acetonitrile (100 mL) were combined and stirred at room temperature under argon for 24 h. The solvent was removed in vacuo and 5% ammonium hydroxide was added. The solution was extracted exhaustively with methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuo to give a solid. Trituration with hexane-ether gave Compound 9 as a solid: 3.5 g (8.0 mmol, 82%)

Workup

  1. customThe solvent was removed in vacuo and 5% ammonium hydroxide
  2. additionwas added
  3. extractionThe solution was extracted exhaustively with methylene chloride
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give a solid

Sources & evidence

ORD record
ord-283d8006fbdf45f99a66a22d31ef67df
Source dataset
uspto-grants-2003_08
Patent number
US06602872B1

Reaction notes

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