Dimethylformamide → 2-Vinyloxyethyl phthalimide

HRID 526276

Reaction equation

HRID 526276 reaction equation
[CH:1]([O:3][CH:4]=[CH2:5])=[CH2:2].C(OCCCl)=C.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:1]([O:3][CH2:4][CH2:5][C:21]1[CH:20]=[CH:19][CH:18]=[C:14]2[C:15]([NH:16][C:12](=[O:22])[C:13]=12)=[O:17])=[CH2:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8024Vinyl etherHCID 80742-Chloroethyl vinyl etherHCID 24194345Phthalimide potassium salt

Product 1

HCID 219723452-Vinyloxyethyl phthalimide

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Vinyl ether monomers for incorporation of amine-containing monomers. 2-Vinyloxy Ethyl Phthalimide was prepared via reacting 2-chloroethyl vinyl ether (25 g, 0.24 mol; CAS #110-75-8) and potassium phthalimide (25 g, 0.135 mol; CAS #1074-82-4) in 100° C. N,N-Dimethylformamide (DMF, 75 ml) using tetra n-butyl ammonium bromide (0.5 g; CAS #1643-19-2) as the phase transfer catalyst. This solution was heated for 6 h 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 6 h
  3. filtrationfiltered
  4. customThis solid was then recrystallized twice from methanol
  5. customto give white crystals

Sources & evidence

ORD record
ord-9e8e39e6734c451382a3ca6e77c6ced6
Source dataset
uspto-grants-2016_05
Patent number
US09345775B2

Linked notes

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