Sodium Hydroxide → Pyridine, 2-(3-chlorophenyl)-6-(4-chlorophenyl)-4-(methylthio)-

HRID 231732

반응식

HRID 231732 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].[CH3:17][S:18][C:19](SC)=[CH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=O.C([O-])(=O)C.[NH4+:36].[OH-].[Na+]>C(O)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:19]([S:18][CH3:17])[CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:36]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 14798Sodium HydroxideHCID 149331-(3-Chlorophenyl)ethanoneHCID 517165Ammonium AcetateHCID 28073791-(4-Chlorophenyl)-3,3-bis(methylsulfanyl)prop-2-en-1-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 189415Pyridine, 2-(3-chlorophenyl)-6-(4-chlorophenyl)-4-(methylthio)-수율 74.7%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

To 20 ml of tetrahydrofuran solution containing 0.60 g of m-chloroacetophenone was added 1.0 g of potassium t-butoxide at room temperature, followed by stirring for 30 minutes. Further, 1 g of 3,3-bis-(methylthio)-1-(4'-chlorophenyl)-2-propen-1-one was added, followed by stirring for 1 hour. Subsequently, 20 ml of acetic acid and 3 g of ammonium acetate were added, and reaction was carried out for 3 hours under reflux, while distilling away tetrahydrofuran. The reaction liquid was neutralized with an aqueous solution of sodium hydroxide, and the neutralized solution was extracted twice with 50 ml portions of ethyl acetate. The extract was dried with anhydrous magnesium sulfate. Ethyl acetate was distilled away under reduced pressure and the residues were recrystallized from isopropanol to give 1.0 g of 2-(3'-chlorophenyl)-4-methylthio-6-(4'-chlorophenyl)pyridine. (m.p. 98.4° C.)

후처리

  1. stirringby stirring for 1 hour
  2. customreaction
  3. waitwas carried out for 3 hours
  4. temperatureunder reflux
  5. distillationwhile distilling away tetrahydrofuran
  6. customThe reaction liquid
  7. extractionthe neutralized solution was extracted twice with 50 ml portions of ethyl acetate
  8. dry with materialThe extract was dried with anhydrous magnesium sulfate
  9. distillationEthyl acetate was distilled away under reduced pressure
  10. customthe residues were recrystallized from isopropanol

출처 및 근거

ORD 기록
ord-909260d93b1f4efa888fa7ce6d7ca364
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04849011

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