Lithium Hydroxide → Diethyl 2-benzoylamino-2-(2-phenylsulfanylethyl)malonate

HRID 2297379

Reaktionsgleichung

Reaktionsgleichung von HRID 2297379
[I-].[Na+].[C:3]1([S:9][CH2:10][CH2:11]Cl)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Li+].[C:15]([NH:23][CH:24]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(C)=O.O.CN1CCCC1=O>[C:15]([NH:23][C:24]([CH2:11][CH2:10][S:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

8

Edukt 4

HCID 3939Lithium HydroxideHCID 5238Sodium IodideHCID 21702((2-Chloroethyl)thio)benzeneHCID 66790Diethyl benzamidomalonate

Produkt 1

HCID 18381758Diethyl 2-benzoylamino-2-(2-phenylsulfanylethyl)malonateAusbeute 17,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A solution comprised of sodium iodide (7.9 g, 52.7 mmol) and 2-chloroethyl phenyl sulfide (4.7 g, 27.2 mmol) in acetone (40 mL) was refluxed for 15 hours. The reaction mixture was cooled, diluted with ice water and extracted with ethyl acetate. The extract was concentrated and the residue was combined with N-methylpyrrolidone (20 mL), lithium hydroxide (1.6 g, 67 mmol) and diethyl 2-benzoylaminomalonate (5 g, 18 mmol). The mixture was stirred at ambient temperature of 15 hours and then poured into cold water. The product was extracted with ethyl acetate and purified by silica gel chromatography to provide diethyl 2-benzoylamino-2-(2-phenylsulfanylethyl)malonate (1.316 g, 3.2 mmol).

Aufarbeitung

  1. temperaturewas refluxed for 15 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated
  5. extractionThe product was extracted with ethyl acetate
  6. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2d69693921f947ef9869edd189980690
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06492362B1

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