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

HRID 2194684

Reaktionsgleichung

Reaktionsgleichung von HRID 2194684
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b039ce92a6a04bf781e802492949995e
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334301B2

Verknüpfte Notizen

Wird geladen…