2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13065112, compound

HRID 1856531Notes

Reaction equation

HRID 1856531 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:18][C:10]2[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11][C:10]=2[CH:18]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13065138HCID 13065138, compound

Product 1

HCID 13065112HCID 13065112, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2.5 g. of 1,2,3,4-tetrahydrodibenzothiophene-3-carboxylic acid ethyl ester in 100 ml. of dioxane was added 4.7 g. of 2,3-dichloro-5,6dicyano-1,4-benzoquinone. The solution was stirred and refluxed for 31 hours. The solution was cooled and the hydroquinone filtered off. The dioxane was removed on a steam bath under reduced pressure. The residue was dissolved in 100 ml. of methylene chloride and the solution passed through a column containing about 75 g. of alumina (Woelm, grade 1). The solvent was removed on a steam bath and the residue crystallized from hexane. The yield of dibenzothiophene-3-carboxylic acid ethyl ester, m.p. 74°-78° was 1.7 g.

Workup

  1. temperaturerefluxed for 31 hours
  2. temperatureThe solution was cooled
  3. filtrationthe hydroquinone filtered off
  4. customThe dioxane was removed on a steam bath under reduced pressure
  5. dissolutionThe residue was dissolved in 100 ml
  6. additioncontaining about 75 g
  7. customThe solvent was removed on a steam bath
  8. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-c266429a7ba34b58b6816d1f295f8f65
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

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