(3-Aminopropyl)triethoxysilane → Bis[2-(2-methacryloyloxyethoxycarbonyl)-ethyl]-(3-triethoxysilylpropyl)amine

HRID 413942Notes

Reaction equation

HRID 413942 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][Si:5]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[C:15]([O:20][CH2:21][CH2:22][O:23][C:24](=[O:27])[CH:25]=[CH2:26])(=[O:19])[C:16]([CH3:18])=[CH2:17].N[SiH3]>C(#N)C>[C:15]([O:20][CH2:21][CH2:22][O:23][C:24]([CH2:25][CH2:26][N:1]([CH2:26][CH2:25][C:24]([O:23][CH2:22][CH2:21][O:20][C:15](=[O:19])[C:16]([CH3:18])=[CH2:17])=[O:27])[CH2:2][CH2:3][CH2:4][Si:5]([O:12][CH2:13][CH3:14])([O:6][CH2:7][CH3:8])[O:9][CH2:10][CH3:11])=[O:27])(=[O:19])[C:16]([CH3:18])=[CH2:17]

Participants

5

Reactant 3

HCID 13521(3-Aminopropyl)triethoxysilaneHCID 14094712CID 14094712HCID 233676582-(Acryloyloxy)ethyl methacrylate

Product 1

HCID 18522489Bis[2-(2-methacryloyloxyethoxycarbonyl)-ethyl]-(3-triethoxysilylpropyl)amineYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

43 g (0.25 mol) 3-aminopropyl triethoxysilane in 40 ml anhydrous acetonitrile are added dropwise accompanied by ice-cooling to 92 g (0.5 mol) 2-acryloyloxyethyl methacrylate in 85 ml acetonitrile. After 48 h stirring at room temperature, the aminosilane has completely reacted. The solvent is evaporated off accompanied by the introduction of air at reduced pressure at the rotary evaporator at maximally 46° C. 132.2 g (98% yield) of a lightly-coloured clear oily liquid are obtained.

Workup

  1. customThe solvent is evaporated off
  2. customaccompanied by the introduction of air at reduced pressure at the rotary evaporator at maximally 46° C

Sources & evidence

ORD record
ord-5289016f25964a41aa630774edf73680
Source dataset
uspto-grants-2003_05
Patent number
US06569917B1

Reaction notes

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