Pyridine → N-methyl-N-(3-trimethoxysilylpropyl)cyanoacetamide

HRID 2374650Notes

Reaction equation

HRID 2374650 reaction equation
[C:1]([CH2:3][C:4](Cl)=[O:5])#[N:2].[CH3:7][NH:8][CH2:9][CH2:10][CH2:11][Si:12]([O:17][CH3:18])([O:15][CH3:16])[O:13][CH3:14].N1C=CC=CC=1>C(OCC)C>[CH3:7][N:8]([CH2:9][CH2:10][CH2:11][Si:12]([O:15][CH3:16])([O:17][CH3:18])[O:13][CH3:14])[C:4](=[O:5])[CH2:3][C:1]#[N:2]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 764801-Propanamine, N-methyl-3-(trimethoxysilyl)-HCID 110515942-Cyanoacetyl chloride

Product 1

HCID 86612158N-methyl-N-(3-trimethoxysilylpropyl)cyanoacetamideYield 77.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a 1 L reactor equipped with a thermometer, a condenser and a loading glass were added 200 mL of diethylether and 11 g of cyanoacetylchloride, followed by stirring at room temperature in the presence of nitrogen. To the reactor were slowly added 20 g of N-methylaminopropyl trimethoxysilane (0.104 mol) and 11 g of pyridine (0.14 mol) in 100 mL of diethylether by using the loading glass. The reaction mixture was stirred for 2 hours at room temperature and then the precipitated pyridine salt was eliminated. After removing the solvent and non-reactants, the reaction mixture was distilled under reduced pressure to give 21 g of N-methyl-N-(3-trimethoxysilylpropyl)cyanoacetamide (formula 3). The yield was 75%.

Workup

  1. customTo a 1 L reactor equipped with a thermometer, a condenser
  2. stirringThe reaction mixture was stirred for 2 hours at room temperature
  3. customAfter removing the solvent and non-reactants
  4. distillationthe reaction mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-ebc5368094154a7d9f32eed08c71fb83
Source dataset
uspto-grants-2008_12
Patent number
US07462663B2

Reaction notes

Loading…