Tetrahydrofuran → 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanethioamide

HRID 2194684

반응식

HRID 2194684 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]#[N:14].C(OCC)(=O)C.Cl.O1CCCC1.P([S-])(OCC)(OCC)=[S:28]>O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13](=[S:28])[NH2:14]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 345881N-(Cyanomethyl)-phthalimideHCID 1385274Diethyl dithiophosphate, potassium saltHCID 21866389Hydrogen chloride-ethyl acetate

생성물 1

HCID 246961282-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanethioamide수율 51%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetonitrile (15 g), a 4 mol/L hydrogen chloride-ethyl acetate solution (40 mL) and tetrahydrofuran (50 mL) was added O,O-diethyl dithiophosphate (15 mL) and the mixture was stirred at room temperature for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate and tetrahydrofuran. The extract was washed twice with water, saturated brine and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as white crystals (yield 9.0 g, yield 51%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate and tetrahydrofuran
  2. washThe extract was washed twice with water, saturated brine and saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-b039ce92a6a04bf781e802492949995e
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334301B2

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