N,N-Dimethylaniline → Triethoxy(3-isocyanatopropyl)silane

HRID 1906972Notes

Reaction equation

HRID 1906972 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].CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[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 949N,N-DimethylanilineHCID 6371PhosgeneHCID 13521(3-Aminopropyl)triethoxysilane

Product 1

HCID 90613Triethoxy(3-isocyanatopropyl)silaneYield 80.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In 150 ml of toluene was dissolved 9.9 g of carbonyl chloride, and a solution of 22.1 g of γ-triethoxysilylpropylamine and 27.9 g of N,N-dimethylaniline in 50 ml of toluene 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 N,N-dimethylaniline chloride was removed by filtration and the filtrate was subjected to distillation to recover toluene, whereby 19.8 g of γ-triethoxysilylpropyl isocyanate was obtained as a fraction having a boiling point of 88° C. to 91° C. under 4.5 mmHg.

Workup

  1. customreaction
  2. customAfter the reaction
  3. customthe crystal of N,N-dimethylaniline chloride was removed by filtration
  4. distillationthe filtrate was subjected to distillation
  5. customto recover toluene

Sources & evidence

ORD record
ord-76eb7fb1b47149afa0821a10779f02ce
Source dataset
uspto-grants-1987_03
Patent number
US04654428

Reaction notes

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