Propargyl bromide → N-prop-2-ynylphthalimide

HRID 2063239Notes

Reaction equation

HRID 2063239 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[C:5]1(=[O:15])[NH:9][C:8](=[O:10])[C:7]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:6]12.[K]>CN(C=O)C.C(OCC)C>[CH2:1]([N:9]1[C:8](=[O:10])[C:7]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:6]2[C:5]1=[O:15])[C:2]#[CH:3]

Participants

5

Reactant 2

HCID 7842Propargyl bromideHCID 24194345Phthalimide potassium salt

Product 1

HCID 81644N-prop-2-ynylphthalimide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Propargyl bromide (1.3 mL, 17.4 mmol) is dissolved in DMF (30 mL) and potassium phtalimide (3.4 g; 18.4 mmol) is added. The mixture is refluxed for 5 h. After cooling at room temperature the mixture is diluted with diethyl ether, washed with water (3×50 mL), dried over Na2SO4 and evaporated under vacuum to give N-propargyl phtalimide as white solid (3.15 g; 17 mmol).

Workup

  1. temperatureThe mixture is refluxed for 5 h
  2. washwashed with water (3×50 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-f7f292e26a1b4e8cbbd67f276c587ee0
Source dataset
uspto-grants-2012_10
Patent number
US08288368B2

Reaction notes

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