p-Toluenesulfonic acid 1-butyn-3-yl ester → 2-(BUT-3-YN-2-YL)ISOINDOLINE-1,3-DIONE

HRID 1648428Notes

Reaction equation

HRID 1648428 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].S(OC(C#C)C)([C:16]1[CH:22]=CC(C)=[CH:18][CH:17]=1)(=O)=O>CN(C=O)C>[C:1]1(=[O:11])[N:5]([CH:17]([C:16]#[CH:22])[CH3:18])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 2

HCID 561098p-Toluenesulfonic acid 1-butyn-3-yl esterHCID 24194345Phthalimide potassium salt

Product 1

HCID 6036332-(BUT-3-YN-2-YL)ISOINDOLINE-1,3-DIONE

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of potassium phthalimide (0.275 mole; 5.1 g) in DMF (20 ml), 2-tosyloxy-3-butyne (0.25 mole) is added and allowed to react for 3 hours at 70° C. After cooling, the reaction mixture is extracted with chloroform and the chloroform layer is washed and dried. Removal of the chloroform, in vacuo, yields crude 2-phthalimido-3-butyne.

Workup

  1. customto react for 3 hours at 70° C
  2. temperatureAfter cooling
  3. extractionthe reaction mixture is extracted with chloroform
  4. washthe chloroform layer is washed
  5. customdried
  6. customRemoval of the chloroform

Sources & evidence

ORD record
ord-54eab44d50f14a9f850665d60a70d295
Source dataset
uspto-grants-1995_07
Patent number
US05436273

Reaction notes

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