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

HRID 2297379

반응식

HRID 2297379 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 18381758Diethyl 2-benzoylamino-2-(2-phenylsulfanylethyl)malonate수율 17.8%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2d69693921f947ef9869edd189980690
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492362B1

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