2-(Dimethylamino)ethyl acrylate → 2-(Acryloyloxy)-N-[(4-benzoylphenyl)methyl]-N,N-dimethylethan-1-aminium bromide

HRID 1709276Notes

Reaction equation

HRID 1709276 reaction equation
[C:1]([O:5][CH2:6][CH2:7][N:8]([CH3:10])[CH3:9])(=[O:4])[CH:2]=[CH2:3].[Br:11][CH2:12][C:13]1[CH:26]=[CH:25][C:16]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:15][CH:14]=1>CC(C)=O>[Br-:11].[C:17]([C:16]1[CH:25]=[CH:26][C:13]([CH2:12][N+:8]([CH3:10])([CH3:9])[CH2:7][CH2:6][O:5][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:14][CH:15]=1)(=[O:18])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 171112-(Dimethylamino)ethyl acrylateHCID 1229514-(Bromomethyl)benzophenone

Product 1

HCID 220625972-(Acryloyloxy)-N-[(4-benzoylphenyl)methyl]-N,N-dimethylethan-1-aminium bromideYield 49.04%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dimethylaminoethyl acrylate (9.11 mls) was added to a stirred solution of 4-bromomethylbenzophenone (13.75g) in acetone (50 mls) at 55° C. and the mixture was stirred for two hours at 60°±2° C. After cooling to room temperature, the stirred mixture was further cooled in an ice bath for two hours prior to filtration. After washing the residue with acetone (X1) followed by isopropyl ether (X2) the solid was dried under vacuo at room temperature. The crude title compound was obtained as a white crystalline solid (14.48g; m.p. 121°-123° C.) which was recrystallised from acetone (150 mls). Filtration, followed by sequentially washing with acetone (X1) then isopropyl ether (X1) and drying under vacuo at room temperature gave the title compound (10.26g; yield =49.04%) as white fine granular crystals of melting point equal to 122°-124° C. Analysis:

Workup

  1. temperaturethe stirred mixture was further cooled in an ice bath for two hours
  2. filtrationto filtration
  3. washAfter washing the residue with acetone (X1)
  4. customwas dried under vacuo at room temperature
  5. customThe crude title compound was obtained as a white crystalline solid (14.48g; m.p. 121°-123° C.) which
  6. customwas recrystallised from acetone (150 mls)
  7. filtrationFiltration
  8. washby sequentially washing with acetone (X1)
  9. dry with materialisopropyl ether (X1) and drying under vacuo at room temperature

Sources & evidence

ORD record
ord-e14e25336fe24562ac81546389c1937c
Source dataset
uspto-grants-1990_08
Patent number
US04948819

Reaction notes

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