Dimethylformamide → 2-Vinyloxyethyl phthalimide

HRID 962352

Reaction equation

HRID 962352 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH:13]([O:15][CH2:16][CH2:17]Cl)=[CH2:14].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:13]([O:15][CH2:16][CH2:17][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:4]([NH:5][C:1](=[O:11])[C:2]=12)=[O:6])=[CH2:14]

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

Conditions

Temperature
100 °C

Procedure

A 1000 ml three-necked flask was charged with potassium phthalimide (100 g, 540 mmol), 2-chloroethyl vinyl ether (100 g, 940 mmol), tetra-n-butylammonium bromide (2 g) and 250 ml dimethylformamide. The reaction mixture was refluxed at 100° C. overnight (approximately 12 hours), with magnetic stirring and under argon atmosphere. After cooling to room temperature, the reaction mixture was poured into 1000 ml of distilled water which precipitates the crude product. Filtration and recrystallization from 3×500 ml methanol and 2×500 ml ethyl acetate with charcoal treatment and drying in the last step with magnesium sulphate gave 55 g (47% based on potassium phthalimide) of the pure 2-vinyloxyethyl phthalimide as slightly yellowish needles. The product was confirmed by 1H NMR (CDCl3) δ (ppm)=3.95 (s,2H+2H+1H), 4.20(d,1H), 6.40(m,1H), 7.70(m,2H), 7.85(m,2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customprecipitates the crude product
  3. filtrationFiltration and recrystallization from 3×500 ml methanol and 2×500 ml ethyl acetate with charcoal treatment
  4. dry with materialdrying in the last step with magnesium sulphate
  5. customgave 55 g (47% based on potassium phthalimide) of the pure 2-vinyloxyethyl phthalimide as slightly yellowish needles

Sources & evidence

ORD record
ord-4831ff2a59064217aa60d2227bafbb56
Source dataset
uspto-grants-1998_06
Patent number
US05759404

Linked notes

Loading…