2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 15841151, compound

HRID 260646Notes

Reaction equation

HRID 260646 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 108996192,3-Dihydro-1-benzofuran-5-sulfonamide

Product 1

HCID 15841151HCID 15841151, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 2,3-dihydrobenzofuran-5-sulfonamide (19.9 g, 100 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (56.7 g, 250 mmol) in dioxane (500 ml) was heated at reflux under nitrogen for 111 hours. The reaction mixture was reduced in volume by evaporation under vacuum and purified by silica gel flash chromatography (EtOAc/hexanes) to provide benzofuran-5-sulfonamide (3.5 g, 18% ) . This was combined with another lot of benzofuran-5-sulfonamide (1.0 g), slurried in ether, collected and vacuum dried at 45° C. overnight to give 4.5 g of benzofuran-5-sulfonamide.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 111 hours
  3. customThe reaction mixture was reduced in volume by evaporation under vacuum
  4. custompurified by silica gel flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-f81ea3fe3b264064b1a502ed3d366e7a
Source dataset
uspto-grants-1996_06
Patent number
US05529999

Reaction notes

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