2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 14722317, compound

HRID 1031668Notes

Reaction equation

HRID 1031668 reaction equation
[CH3:1][O:2][CH:3]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][C:6]=2[O:5][CH2:4]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][C:6]=2[O:5][CH:4]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14722453HCID 14722453, compound

Product 1

HCID 14722317HCID 14722317, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

There were mixed 3.63 g of 2,3-dihydro-3-methoxy-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran4-one, 3.41 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 150 ml of dioxane. The mixture was refluxed for 48 hours. The reaction mixture was cooled. The resulting precipitate was removed by filtration. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 3 : 1 mixture of toluene and ethyl acetate) to obtain 1.91 g (yield: 52.9%) of 3-methoxy-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one [Compound No. 2].

Workup

  1. temperatureThe mixture was refluxed for 48 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe resulting precipitate was removed by filtration
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by a column chromatography (eluant
  6. additiona 3 : 1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-d28791e6ede9425e88289421b912d920
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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