2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Benzenesulfonyl-naphthalene-1-carbonitrile

HRID 1715051Notes

Reaction equation

HRID 1715051 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]#[N:21])=[CH:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]#[N:21])=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O: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-benzoquinone2×HCID 590217566-Benzenesulfonyl-3,4-dihydro-naphthalene-1-carbonitrile

Product 1

HCID 590287716-Benzenesulfonyl-naphthalene-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.89 g (3 mmoles) 6-benzenesulfonyl-3,4-dihydro-naphthalene-1-carbonitrile and 0.68 g (3 mmoles) DDQ in 15 mL dioxane was heated under reflux for 18 hours. Another 0.25 g (0.12 mmole) DDQ was added and the reaction mixture was heated under reflux for another 20 hours. The mixture was filtered and the collected solids were washed with diethyl ether. The filtrate was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and washed with 5% sodium hydroxide and half-saturated aqueous sodium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to column chromatography over silica gel 230-400 mesh eluting with chloroform:hexane:ethyl acetate (50:49:1), then with 50:48:2 and finally with 50:46:4. The title compound was obtained as a white solid, 0.266 gram (30%). NMR (CDCl3) ppm δ: 8.67 (d, 1H, J=1.8 Hz), 8.34 (d, 1H, J=8.8 Hz), 8.24 (d, 1H, J=8.41 Hz), 8.04 (m, 4H), 7.69 (dd, 1H, J=4.25 Hz, J=11.5 Hz), 7.56 (m 3H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for another 20 hours
  5. filtrationThe mixture was filtered
  6. washthe collected solids were washed with diethyl ether
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. washwashed with 5% sodium hydroxide and half-saturated aqueous sodium chloride
  10. dry with materialThe organic phase was dried (magnesium sulfate)
  11. concentrationconcentrated under reduced pressure
  12. washeluting with chloroform:hexane:ethyl acetate (50:49:1)

Sources & evidence

ORD record
ord-0720fb266bb04f48a7c9b502af371f38
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

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