Methacryloyl chloride → Aminoethyl methacrylate hydrochloride

HRID 1242842Notes

Reaction equation

HRID 1242842 reaction equation
Cl.[CH2:2]([CH2:4][NH2:5])[OH:3].[C:6]([Cl:11])(=[O:10])[C:7]([CH3:9])=[CH2:8]>C1(C)C=CC=CC=1>[ClH:11].[CH3:9][C:7](=[CH2:8])[C:6]([O:3][CH2:2][CH2:4][NH2:5])=[O:10]

Participants

4

Reactant 2

HCID 13528Methacryloyl chlorideHCID 74819Ethanolamine Hydrochloride

Product 1

HCID 75495Aminoethyl methacrylate hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

In a 500 mL three-neck flask equipped with a thermometer and a reflux condenser were placed 300 g of toluene and 60.0 g (0.62 mol) of ethanolamine hydrochloride, followed by heating to 110° C. with stirring. After the inner temperature reached 110° C., 77.1 g (0.74 mol) of methacryloyl chloride was added dropwise thereto over a period of 30 minutes. After completion of the dropwise addition, the mixture was continued to stir for further 3 hours and then cooled to 0° C. with stirring. The precipitated solid was collected by filtration and then the resulting solid was washed with 300 g of diisopropyl ether. The solid was collected by filtration and then dried under reduced pressure to obtain 85.2 g of 2-aminoethyl 2-methylacrylate hydrochloride.

Workup

  1. customIn a 500 mL three-neck flask equipped with a thermometer and a reflux condenser
  2. customreached 110° C.
  3. additionAfter completion of the dropwise addition
  4. stirringto stir for further 3 hours
  5. temperaturecooled to 0° C.
  6. stirringwith stirring
  7. filtrationThe precipitated solid was collected by filtration
  8. washthe resulting solid was washed with 300 g of diisopropyl ether
  9. filtrationThe solid was collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-51c7103a3a9d4debb4a89eef46b8e5d7
Source dataset
uspto-grants-2006_10
Patent number
US07115771B2

Reaction notes

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