Phthalimide → N-(3-Buten-1-yl)phthalimide

HRID 1626306Notes

Reaction equation

HRID 1626306 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.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH:21]=[CH2:22]>C(#N)C>[CH2:22]([N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6])[CH2:21][CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 339432N-(3-Buten-1-yl)phthalimideYield 49.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of phthalimide (3.92 g, 26.6 mmol) and potassium carbonate (9.20 g, 66.6 mmol) in acetonitrile (44 ml), was added 4-bromo-1-butene (2.26 ml, 22.2 mmol) at room temperature. The resulting reaction mixture was stirred at 90° C. for 13 hours. After the reaction complete, the reaction mixture thus obtained was filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to obtain the title compound (2.23 g). The compound was used for the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customAfter the reaction complete, the reaction mixture thus obtained
  3. filtrationwas filtered through a plug of Celite
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9dfd49463b8e4eefa43a9351bcd977d2
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

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