Hydrogen Sulfide → 2-(2'-Chloro-4'-aminophenyl)-5,5-dimethyl-1,3-cyclohexanedione
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
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, then 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 collect and carefully acidified to pH=4 with 6N HCl. A white solid formed which was collected by suction filtration to give 13.3 g (74%) of 2-(2'-Chloro-4'-aminophenyl)-5,5-dimethyl-1,3-cyclohexanedione, m.p. 218°-19° C.
Workup
- customwas absorbed
- temperaturethe temperature was raised to the reflux point and H2S
- filtrationThe reaction mixture was filtered
- customto remove sulfur
- customthe filtrate evaporated under reduced pressure
- additionTo the residue was added 300 ml of 0.25N NaOH
- filtrationthe solution filtered once more
- customThe filtrate was collect
- customA white solid formed which
- filtrationwas collected by suction filtration
Sources & evidence
- ORD record
- ord-f6b7d8b308a74a7694e3916fc3702206
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04659372
Reaction notes
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