Dimethylformamide → 2-Vinyloxyethyl phthalimide

HRID 2245187Notes

Reaction equation

HRID 2245187 reaction equation
[CH:1]([O:3][CH2:4][CH2:5]Cl)=[CH2:2].[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.[K].CN(C=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:1]([O:3][CH2:4][CH2:5][C:16]1[CH:15]=[CH:14][CH:13]=[C:9]2[C:10]([NH:11][C:7](=[O:17])[C:8]=12)=[O:12])=[CH2:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 80742-Chloroethyl vinyl etherHCID 24194345Phthalimide potassium salt

Product 1

HCID 219723452-Vinyloxyethyl phthalimide

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

2-Vinyloxy Ethyl Phthalimide was prepared via reacting 2-chloroethyl vinyl ether (25 g, 0.24 mol) and potassium phthalimide (25 g, 0.135 mol) in 100° C. DMF(75 mL) using tetra n-butyl ammonium bromide (0.5 g) as the phase transfer catalyst. This solution was heated for six hours and then crashed out in water and filtered. This solid was then recrystallized twice from methanol to give white crystals.

Workup

  1. customin 100° C
  2. temperatureThis solution was heated for six hours
  3. filtrationfiltered
  4. customThis solid was then recrystallized twice from methanol
  5. customto give white crystals

Sources & evidence

ORD record
ord-2d57f36f1efd4792bcf38681f4d99180
Source dataset
uspto-grants-2010_03
Patent number
US07682626B2

Reaction notes

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