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

HRID 65288노트

반응식

HRID 65288 반응식
[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]

참가 물질

5

반응물 2

HCID 402Hydrogen Sulfide2회HCID 128766182-(2'-Chloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexandione

생성물 1

HCID 128765962-(2'-Chloro-4'-aminophenyl)-5,5-dimethyl-1,3-cyclohexanedione수율 74.7%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 14923Ammonium Hydroxide용매

실험 절차

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 6NHCl. 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°-219° C.

후처리

  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. customA white solid formed which
  10. filtrationwas collected by suction filtration

출처 및 근거

ORD 기록
ord-e2822c982328476c904f25740f3934ae
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04613617

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