(3-Aminopropyl)triethoxysilane → HCID 58903422, compound

HRID 1051973Notes

Reaction equation

HRID 1051973 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].Cl[CH2:16][CH2:17][N:18]=[C:19]=[O:20].[C:21]([O-])(=[S:23])C.[K+]>C(O)C>[Si:5]([CH2:4][CH2:3][CH2:2][NH:1][C:19]([NH:18][CH2:17][CH2:16][S:23][CH3:21])=[O:20])([O:12][CH2:13][CH3:14])([O:6][CH2:7][CH3:8])[O:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 13521(3-Aminopropyl)triethoxysilaneHCID 160352-Chloroethyl isocyanateHCID 23670855Potassium ethanethioate

Product 1

HCID 58903422HCID 58903422, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-78 °C

Procedure

3-Aminopropyltriethoxysilane (132.82 g, 0.60 mol, 1.00 eq) is initially charged in ethanol (300 ml) in a three-neck flask with precision glass stirrer, internal thermometer, dropping funnel and reflux condenser, and cooled to −78° C. 2-Chloroethyl isocyanate (63.34 g, 0.60 mol, 1.00 eq) is added dropwise at −78 to −68° C. within 1.75 h and then the mixture is heated to 50° C. Potassium thioacetate (68.53 g, 0.60 mol, 1.00 eq) is added in five portions and the mixture is heated to reflux. After a reaction time of 2.25 h, the mixture is cooled to room temperature and the suspension is filtered. The filtrate is freed of the solvent on a rotary evaporator and dried under reduced pressure. The (EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—S—CH3 product (213.91 g, 97.3% of theory) is obtained as a waxy white solid.

Workup

  1. temperaturereflux condenser
  2. temperaturethe mixture is heated to 50° C
  3. temperaturethe mixture is heated to reflux
  4. temperatureAfter a reaction time of 2.25 h, the mixture is cooled to room temperature
  5. filtrationthe suspension is filtered
  6. customThe filtrate is freed of the solvent on a rotary evaporator
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-b93823ef77834618a5ec19a36ee90ed6
Source dataset
uspto-grants-2016_07
Patent number
US09388200B2

Reaction notes

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