Dimethylformamide → 2-Vinyloxyethyl phthalimide

HRID 1471304Notes

Reaction equation

HRID 1471304 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)C=O>[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; 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-4f926c5af7a04e2888ea67d8e4bb372b
Source dataset
uspto-grants-2015_04
Patent number
US09011919B2

Reaction notes

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