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

HRID 1828368노트

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HRID 1828368 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

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.).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f8e1646f0e34531846a954fcc0b286f
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07057067B2

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