Phthaloyl chloride → 2-Ethanethioylisoindoline-1,3-dione

HRID 2224739Notes

Reaction equation

HRID 2224739 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:11](Cl)(=[O:21])[C:12]1[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:14](Cl)=[O:15]>O1CCCC1>[C:1]([N:4]1[C:14](=[O:15])[C:13]2[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]1=[O:21])(=[S:3])[CH3:2]

Participants

5

Reactant 3

HCID 6955Phthaloyl chlorideHCID 11430Potassium CarbonateHCID 2723949Thioacetamide

Product 1

HCID 451186352-Ethanethioylisoindoline-1,3-dioneYield 13.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of thioacetamide (10.04 g, 133.6 mmol) and potassium carbonate (45.80 g, 331.4 mmol) in 100 mL tetrahydrofuran at 0° C. add phthaloyl chloride (28.49 g, 140.3 mmol) dropwise. Raise the reaction temperature to 25° C. after 2 hours and allow it to stir for an additional 2 hours before cooling the reaction mixture to 0° C. again. Quench the reaction by adding 125 mL of ice water dropwise. Extract the reaction mixture with EtOAc (2×). Dry the organic layer with magnesium sulfate and remove the solvent in vacuo to yield 3.7 g of 2-thioacetylisoindole-1,3-dione as a crude reddish solid. See also J. Org. Chem. 1997, 62, 3808-3809. 1H NMR (CDCl3) δ 8.00 (2 H, m), 7.82 (2 H, m), 3.10 (3 H, s).

Workup

  1. temperaturebefore cooling the reaction mixture to 0° C. again
  2. customQuench
  3. customthe reaction
  4. extractionExtract the reaction mixture with EtOAc (2×)
  5. dry with materialDry the organic layer with magnesium sulfate
  6. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-d11fa0566fb74e1789a88f6c734de600
Source dataset
uspto-grants-2008_05
Patent number
US07378447B2

Reaction notes

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