N-methyl-2-pyrrolidone → Methyl 3-iodo-2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)-benzoate

HRID 1828368ノート

反応式

HRID 1828368 の反応式
[I:1]N1C(C)(C)C(=O)N(I)C1=O.[CH3:12][C:13]([NH:19][C:20]([C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25])=[O:21])([CH3:18])[CH2:14][S:15]([CH3:17])=[O:16].CN1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[I:1][C:31]1[C:22]([C:20]([NH:19][C:13]([CH3:12])([CH3:18])[CH2:14][S:15]([CH3:17])=[O:16])=[O:21])=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25]

参加物

6

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 2005341,3-Diiodo-5,5-dimethylimidazolidine-2,4-dioneHCID 69343931Methyl 2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)benzoate

生成物 1

HCID 12010603Methyl 3-iodo-2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)-benzoate収率 137.3%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

Into the same reactor as in Example 1 were charged 1.5 mg of palladium acetate, 0.83 g of 1,3-diiodo-5,5-dimethylhydantoin, 1.0 g of methyl 2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)benzoate and 5 ml of N-methylpyrrolidone. The mixture thus obtained was heated with stirring at 90° C. for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and poured into water, and the objective product was extracted with ethyl acetate. The organic layer was washed successively with aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. By distilling off the solvent under reduced pressure, a crude product was obtained. Purification of the crude product by silica gel column chromatography (ethyl acetate/n-hexane=1/3) gave 1.27 g of methyl 3-iodo-2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)-benzoate (yield 89.1%, melting point 150.7–151.8° C.).

後処理

  1. customThe mixture thus obtained
  2. temperaturewas heated
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled to room temperature
  5. extractionthe objective product was extracted with ethyl acetate
  6. washThe organic layer was washed successively with aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationBy distilling off the solvent under reduced pressure
  9. customa crude product was obtained
  10. customPurification of the crude product by silica gel column chromatography (ethyl acetate/n-hexane=1/3)

出典と根拠

ORDレコード
ord-7f8e1646f0e34531846a954fcc0b286f
出典データセット
uspto-grants-2006_06
特許番号
US07057067B2

反応ノート

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