Triethylamine → 2-Methyl-N-[3-(triethoxysilyl)propyl]acrylamide

HRID 1074215Notes

Reaction equation

HRID 1074215 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(N(CC)CC)C.[C:22](Cl)(=[O:26])[C:23]([CH3:25])=[CH2:24]>C1(C)C=CC=CC=1>[C:22]([NH:1][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:26])[C:23]([CH3:25])=[CH2:24]

Participants

5

Conditions

Temperature
0 °C

Procedure

A solution of 3-aminopropyltriethoxysilane (20.0 g) in toluene (200 ml) was added to a 500 ml three neck flask equipped with magnetic stir bar, addition funnel, and nitrogen inlet. A total of 9.11 g of triethylamine was added to the solution and the solution was cooled to 0° C. in an ice bath. A total of 9.41 g of methacryloyl chloride was added dropwise to the reaction by the addition funnel at a rate such that the temperature did not exceed 5° C. The reaction was stirred overnight with gradual warming to room temperature. The reaction mixture was then washed 4 times with 200 ml of ice water, dried over magnesium sulfate and concentrated under vacuum. The yield was 38.4 percent and the reaction product was used without further purification.

Workup

  1. customequipped with magnetic stir bar, addition funnel, and nitrogen inlet
  2. customdid not exceed 5° C
  3. temperaturewith gradual warming to room temperature
  4. washThe reaction mixture was then washed 4 times with 200 ml of ice water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe yield was 38.4 percent and the reaction product was used without further purification

Sources & evidence

ORD record
ord-e3795e7e93fd4cda865327ab99985853
Source dataset
uspto-grants-1990_11
Patent number
US04973680

Reaction notes

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