Hydrogen Sulfide → 2-(2'-Chloro-4'-aminophenyl)-5,5-dimethyl-1,3-cyclohexanedione

HRID 127547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 127547
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH:11]1[C:16](=[O:17])[CH2:15][C:14]([CH3:19])([CH3:18])[CH2:13][C:12]1=[O:20].S>[OH-].[NH4+].C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH:11]1[C:16](=[O:17])[CH2:15][C:14]([CH3:18])([CH3:19])[CH2:13][C:12]1=[O:20]

Komponenten

5

Edukt 2

HCID 402Hydrogen Sulfide2×HCID 128766182-(2'-Chloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexandione

Produkt 1

HCID 128765962-(2'-Chloro-4'-aminophenyl)-5,5-dimethyl-1,3-cyclohexanedione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 20.0 g (0.067 mol) of 2-(2'-chloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexanedione in 150 ml of concentrated ammonium hydroxide and 150 ml of ethanol was stirred at room temperature while passing hydrogen sulfide gas through the solution at such a rate that all of the H2S was absorbed. When the solution was saturated with H2S, the temperature was raised to the reflux point and H2S continuously passed slowly through the refluxing solution for 24 hours. The reaction mixture was filtered to remove sulfur, and the filtrate evaporated under reduced pressure. To the residue was added 300 ml of 0.25 N NaOH, and the solution filtered once more. The filtrate was cooled and carefully acidified to pH=4 with 6 N HCl. 2-(2'-Chloro-4'-aminophenyl)-5,5-dimethyl-1,3-cyclohexanedione was collected by suction filtration.

Aufarbeitung

  1. customwas absorbed
  2. temperaturethe temperature was raised to the reflux point and H2S
  3. filtrationThe reaction mixture was filtered
  4. customto remove sulfur
  5. customthe filtrate evaporated under reduced pressure
  6. additionTo the residue was added 300 ml of 0.25 N NaOH
  7. filtrationthe solution filtered once more
  8. temperatureThe filtrate was cooled
  9. filtration2-(2'-Chloro-4'-aminophenyl)-5,5-dimethyl-1,3-cyclohexanedione was collected by suction filtration

Quellen und Nachweise

ORD-Eintrag
ord-263bf9a698164048944e99e3403981ee
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256657

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