Diethyl Ether → HCID 13725713, compound

HRID 1168552Notes

Reaction equation

HRID 1168552 reaction equation
[CH3:1][C:2]([C:4]([O:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10])=[O:5])=[CH2:3].[CH3:12][S:13]([O:16]C)(=[O:15])=[O:14].[C:18]([O-])(=O)C(C)=C.CCOCC>C(#N)C>[CH3:12][S:13]([O-:16])(=[O:15])=[O:14].[C:4]([O:6][CH2:7][CH2:8][N+:9]([CH3:18])([CH3:11])[CH3:10])(=[O:5])[C:2]([CH3:1])=[CH2:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 4156Methyl MethanesulfonateHCID 17869(Dimethylamino)ethyl methacrylateHCID 87595Methacrylate

Product 1

HCID 13725713HCID 13725713, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

3.14 g (20 mmol) DMAEMA was dissolved in 30 ml acetonitrile and 1.7 ml (2.203 g, 20 mmol) methyl methanesulfonate was added. The mixture was heated to 90° C. (reflux) with stirring for 24 h. At the end of the reaction period the mixture becomes viscous, indicating probably some polymerization of the methacrylate. The mixture was poured into 400 ml ether, and the precipitate was filtered and washed with ether, then dried in vacuo. The obtained salt is very hygroscopic. It contains a small amount of polymer, so this synthesis will be done again in the presence of inhibitor of polymerization, which can be removed after the reaction. Yield: 3.50 g (65%)

Workup

  1. temperature(reflux)
  2. customAt the end of the reaction period the mixture
  3. filtrationthe precipitate was filtered
  4. washwashed with ether
  5. customdried in vacuo
  6. customso this synthesis
  7. customwill be done again in the presence of inhibitor of polymerization, which
  8. customcan be removed
  9. customafter the reaction

Sources & evidence

ORD record
ord-24ca8f6e48d64a24b6f7e42bbe651255
Source dataset
uspto-grants-2003_09
Patent number
US06624262B2

Reaction notes

Loading…