Dimethylformamide → 2-Vinyloxyethyl phthalimide

HRID 1160045Notes

Reaction equation

HRID 1160045 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-ab2395295ecd4cbab59914a12044659a
Source dataset
uspto-grants-2010_10
Patent number
US07816337B2

Reaction notes

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