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

HRID 1670881Notes

Reaction equation

HRID 1670881 reaction equation
[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.CCOP(S)(OCC)=[S:31]>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:31])[NH2:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9274O,O-Diethyl dithiophosphateHCID 345881N-(Cyanomethyl)-phthalimideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetonitrile (15 g), 4 mol/L hydrogen chloride-ethyl acetate solution (40 mL) and tetrahydrofuran (50 mL) was added O,O-diethyldithiophosphate (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, and then washed with 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, 51%).

Workup

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

Sources & evidence

ORD record
ord-bc0390564de545e5adb268323abbc0da
Source dataset
uspto-grants-2011_08
Patent number
US07994205B2

Reaction notes

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