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

HRID 2297379

反応式

HRID 2297379 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 18381758Diethyl 2-benzoylamino-2-(2-phenylsulfanylethyl)malonate収率 17.8%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2d69693921f947ef9869edd189980690
出典データセット
uspto-grants-2002_12
特許番号
US06492362B1

関連ノート

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