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

HRID 65273Notes

Reaction equation

HRID 65273 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

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 0.25N NaOH, and the solution filtered once more. The filtrate was cooled and carefully acidified to pH=4 with 6N HCl. 2-(2'-Chloro-4'-aminophenyl)-5,5-dimethyl-1,3-cyclohexanedione was collected by suction filtration.

Workup

  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 0.25N 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

Sources & evidence

ORD record
ord-f575fa33aeac4bd79cb4f4118f2b6439
Source dataset
uspto-grants-1986_09
Patent number
US04613617

Reaction notes

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