Water → 2-[2-(3-Thienyl)ethyl]-1H-isoindole-1,3(2H)-dione

HRID 611231Notes

Reaction equation

HRID 611231 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)(=O)=O.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K].O>CN(C)C=O>[S:10]1[CH:11]=[CH:12][C:8]([CH2:7][CH2:6][N:17]2[C:16](=[O:18])[C:15]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]3[C:13]2=[O:23])=[CH:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 144229343-Thiopheneethanol methanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 217846452-[2-(3-Thienyl)ethyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the above crude 2-(3-thienyl)ethyl methanesulfonate in 400 ml of N,N-dimethylformamide, 12.8 g (69.0 mmol) of potassium phthalimide was added, followed by overnight stirring at 100° C. After cooling to room temperature, the reaction mixture was added to water with vigorous stirring. The resulting precipitate was filtered, washed with water and dried to yield the desired product.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-43675b1f01b74f1db3ff14ff622eb9b9
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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