2-(Dimethylamino)ethyl acrylate → HCID 23037626, compound

HRID 1709278Notes

Reaction equation

HRID 1709278 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:14]=[C:15]([CH:24]=[CH:25][CH:26]=1)[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]>C(OCC)(=O)C>[Br-:11].[C:16]([C:15]1[CH:14]=[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:26]=[CH:25][CH:24]=1)(=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 171112-(Dimethylamino)ethyl acrylateHCID 895863-(Bromomethyl)benzophenone

Product 1

HCID 23037626HCID 23037626, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Dimethylaminoethyl acrylate (11.4 mls) was added to a stirred solution of 3-bromomethylbenzophenone (20.6g) in ethyl acetate (100 mls) at 60° C. and the mixture stirred for 1 hour at 60° C. After cooling to room temperature the mixture was stirred for 1 hour prior to filtration. After washing the residue with ethyl acetate (3x) the solid was dried under vacuo at room temperature. The crude title compound was obtained as a cream solid (27.3g, MP 165°-168° C.) which was recrystallised from propan-2-ol/isopropyl ether. Filtration followed by washing with isopropyl ether then drying under vacuo at room temperature gave the title compound as pale cream crystals. (20.2g, yield =64.5%, MP 168°-169° C.).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. stirringwas stirred for 1 hour
  3. filtrationto filtration
  4. washAfter washing the residue with ethyl acetate (3x) the solid
  5. customwas dried under vacuo at room temperature

Sources & evidence

ORD record
ord-fdfe3350f58c4273aea71803a6b6670d
Source dataset
uspto-grants-1990_08
Patent number
US04948819

Reaction notes

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