Triethylamine → 3-(Triethoxysilyl)propylacrylamide

HRID 54885

Reaction equation

HRID 54885 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].N[CH2:7][CH2:8][CH2:9][Si:10]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].C([N:22](CC)CC)C>ClCCl>[CH2:12]([O:11][Si:10]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])[CH2:9][CH2:8][CH2:7][C:2](=[CH2:3])[C:1]([NH2:22])=[O:4])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 13521(3-Aminopropyl)triethoxysilane

Product 1

HCID 187622113-(Triethoxysilyl)propylacrylamideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of acryloyl chloride (8.5 mL, 105 mmol) in dry dichloromethane (250 mL) cooled to 0° C. was added dropwise a mixture of 3-aminopropyltriethoxysilane (23.5 mL, 100 mmol) and triethylamine (13.9 mL, 100 mmol) in dichloromethane (50 mL). After completion of addition the reaction mixture was stirred for 30 min, then filtered. The filtrate was concentrated to an oil, diluted with hexane (100 mL) and filtered. The resulting filtrate was concentrated to oil and distilled in vacuo. The product was obtained as a viscous liquid (21.2 g, 77%), b.p. 142-145/1 mm Hg.

Workup

  1. additionwas added dropwise
  2. additionAfter completion of addition the reaction mixture
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to an oil
  5. additiondiluted with hexane (100 mL)
  6. filtrationfiltered
  7. concentrationThe resulting filtrate was concentrated to oil
  8. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-002083350cc34e8dbe3e7428d2f0b9f3
Source dataset
uspto-grants-1997_04
Patent number
US05624711

Linked notes

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