Pyridine → Triethoxy(3-isocyanatopropyl)silane

HRID 1906974Notes

Reaction equation

HRID 1906974 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([O:7][Si:8]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])[CH2:9][CH2:10][CH2:11][NH2:12])[CH3:6].N1C=CC=CC=1>C(OCC)C>[CH2:14]([O:13][Si:8]([O:16][CH2:17][CH3:18])([O:7][CH2:5][CH3:6])[CH2:9][CH2:10][CH2:11][N:12]=[C:1]=[O:2])[CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 13521(3-Aminopropyl)triethoxysilane

Product 1

HCID 90613Triethoxy(3-isocyanatopropyl)silaneYield 70.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In 150 ml of ethyl ether was dissolved 9.9 g of carbonyl chloride, and a solution of 22.1 g of γ-triethoxysilylpropylamine and 18.2 g of pyridine in 50 ml of ethyl ether was dropped into the above solution at -5° C. to -10° C. over a period of 3 hours to effect reaction. After the reaction, the crystal of pyridine hydrochloride was removed by filtration and the filtrate was distilled to recover ethyl ether, whereby 17.3 g of γ-triethoxysilylpropyl isocyanate was obtained as a fraction having a boiling point of 95° C. to 100° C. under 8 mmHg.

Workup

  1. customreaction
  2. customAfter the reaction
  3. customthe crystal of pyridine hydrochloride was removed by filtration
  4. distillationthe filtrate was distilled
  5. customto recover ethyl ether

Sources & evidence

ORD record
ord-15c8711211a54f6faac01c8e81fc3cb0
Source dataset
uspto-grants-1987_03
Patent number
US04654428

Reaction notes

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