2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-(4-Phenylsulfonyl-butoxy)-carbostyril

HRID 1065369Notes

Reaction equation

HRID 1065369 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[C:15]1([S:21]([CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[CH2:31][CH2:32][C:33](=[O:39])[NH:34]3)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1>[C:15]1([S:21]([CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[CH:31]=[CH:32][C:33](=[O:39])[NH:34]3)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 205400365-(4-Phenylsulfonyl-butoxy)-3,4-dihydro-carbostyril

Product 1

HCID 205400375-(4-Phenylsulfonyl-butoxy)-carbostyril

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.87 gm of 2,3-dichloro-5,6-dicyano-benzoquinone were added to a solution of 1.8 gm of 5-(4-phenylsulfonyl-butoxy)-3,4-dihydro-carbostyril in 45 ml of dioxane, and the solution was boiled for 2.5 hours on an oil bath. The reaction mixture was then filtered while still hot, and the insoluble matter, which was formed during the reaction was washed with hot dioxane. The combined filtrates were diluted with 100 ml of chloroform and extracted several times with altogether 150 ml of 2N sodium hydroxide. After drying the chloroform extracts with sodium sulfate and filtering in the presence of activated charcoal, the filtrate was concentrated by evaporation, and ethyl acetate was added until white crystals were precipitated.

Workup

  1. filtrationThe reaction mixture was then filtered while still hot, and the insoluble matter
  2. customwhich was formed during the reaction
  3. washwas washed with hot dioxane
  4. additionThe combined filtrates were diluted with 100 ml of chloroform
  5. extractionextracted several times with altogether 150 ml of 2N sodium hydroxide
  6. dry with materialAfter drying the chloroform
  7. filtrationfiltering in the presence of activated charcoal
  8. concentrationthe filtrate was concentrated by evaporation, and ethyl acetate
  9. additionwas added until white crystals
  10. customwere precipitated

Sources & evidence

ORD record
ord-22ca3da23c64411fb25371e1456b880d
Source dataset
uspto-grants-1982_05
Patent number
US04329347

Reaction notes

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