2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 12789651, compound

HRID 1856368Notes

Reaction equation

HRID 1856368 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[O:11][N:10]=[C:9]([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])[CH2:8]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClC1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])[CH:8]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12789645HCID 12789645, compound

Product 1

HCID 12789651HCID 12789651, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 11.0 g (0.039 mol) of methyl 2-[5-(2-pyridyl)-2-isoxazolin-3-yl]benzoate and 9.76 g (0.043 mol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in 200 ml of chlorobenzene was held at reflux for 3 hours; the mixture was allowed to cool, was filtered, and was concentrated under vacuum to 12.0 g of residue. The residue was chromatographed on 400 g of silica gel with 20% ether in benzene to give 3.8 g (35%) of solid, mp 54°-57° C. Recrystallization of a small sample gave solid with mp 58°-60.5° C.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureto cool
  3. filtrationwas filtered
  4. concentrationwas concentrated under vacuum to 12.0 g of residue
  5. customThe residue was chromatographed on 400 g of silica gel with 20% ether in benzene

Sources & evidence

ORD record
ord-d156931c48ad4fb5a8603d3f54649958
Source dataset
uspto-grants-1980_08
Patent number
US04219351

Reaction notes

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