Water → N-[[5-(1,3-Dioxolan-2-yl)-4-methyl-2-thienyl]-4-butyl]isoindole-1,3(2H)-dione

HRID 867933Notes

Reaction equation

HRID 867933 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[S:10][C:9]([CH:11]2[O:15][CH2:14][CH2:13][O:12]2)=[C:8]([CH3:16])[CH:7]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K].O>CN(C)C=O>[O:12]1[CH2:13][CH2:14][O:15][CH:11]1[C:9]1[S:10][C:6]([CH:5]([N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])[CH2:4][CH2:3][CH3:2])=[CH:7][C:8]=1[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 129265212-[5-(4-Bromobutyl)-3-methyl-2-thienyl]-1,3-dioxolaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 21289071N-[[5-(1,3-Dioxolan-2-yl)-4-methyl-2-thienyl]-4-butyl]isoindole-1,3(2H)-dioneYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[5-(4-Bromobutyl)-3-methyl-2-thienyl]-1,3-dioxolane (13.3 g) and potassium phthalimide (8.9 g) were stirred at 50° in dry dimethylformamide (130 ml) for 4 h and then at room temperature for 18 h. The mixture was poured into water (1500 ml) and extracted with ether. The organic extract was evaporated to give the title compound as a light yellow oil (16.1 g)

Workup

  1. extractionextracted with ether
  2. extractionThe organic extract
  3. customwas evaporated

Sources & evidence

ORD record
ord-31faf40c4d6e4ce9ad05ad32216c918e
Source dataset
uspto-grants-1988_10
Patent number
US04777179

Reaction notes

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