Phthalimide → Phthalimide, N-(3-methyl-2-butenyl)-

HRID 2408353Notes

Reaction equation

HRID 2408353 reaction equation
Br[CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12>CN(C=O)C>[CH3:5][C:4]([CH3:6])=[CH:3][CH2:2][N:11]1[C:7](=[O:17])[C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]1=[O:12]

Participants

4

Reactant 2

HCID 6809PhthalimideHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 96648Phthalimide, N-(3-methyl-2-butenyl)-Yield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 g of 1-bromo-3-methylbut-2-ene and 26.1 g of phthalimide are suspended in anhydrous DMF, and then the mixture is refluxed for 12 h with heating. After returning to RT, the reaction medium is filtered and then taken up with an aqueous solution saturated with NH4Cl. The aqueous phase is extracted with AcOEt, washed with a solution of NaCl, and then dried on magnesium sulfate and dry evaporated. The obtained solid is suspended in 100 mL of water and stirred. The precipitated product is filtered, rinsed with ether and then dried in the oven in vacuo at 65° C. 18.3 g (yield=63%) of 2-(3-methylbut-2-en-1-yl)-1H-isoindole-1,3-dione are obtained as a white powder used as such.

Workup

  1. temperaturethe mixture is refluxed for 12 h
  2. temperaturewith heating
  3. customAfter returning to RT
  4. filtrationthe reaction medium is filtered
  5. extractionThe aqueous phase is extracted with AcOEt
  6. washwashed with a solution of NaCl
  7. customdried on magnesium sulfate
  8. customdry
  9. customevaporated
  10. filtrationThe precipitated product is filtered
  11. washrinsed with ether
  12. customdried in the oven in vacuo at 65° C

Sources & evidence

ORD record
ord-a76df9b083874170885831a2e1cfb51f
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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