(3-Aminopropyl)triethoxysilane → HCID 131736108, compound

HRID 1051976Notes

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

Participants

Conditions

Temperature: -78 °C

Procedure

In a first reaction step, 3-aminopropyltriethoxysilane (159.39 g, 0.72 mol, 1.00 eq) is initially charged in ethanol (3.0 l) in a 4 l three-neck flask with precision glass stirrer, internal thermometer, dropping funnel and reflux condenser, and cooled to −78° C. 2-Chloroethyl isocyanate (75.92 g, 0.72 mol, 1.00 eq) is added dropwise at −78 to −69° C. within 2.25 h and then the mixture is heated to 50° C. Dry sodium sulphide (Na2S, 28.09 g, 0.36 mol, 0.50 eq) is added in five portions and the mixture is heated to reflux. After a reaction time of 4.5 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—CH2CH2—NH—CO—NH—CH2CH2CH2—Si(OEt)3 product (214.09 g, 96.7% of theory) is obtained as a waxy, white solid.

Workup

temperaturereflux condenser
temperaturethe mixture is heated to 50° C
temperaturethe mixture is heated to reflux
temperatureAfter a reaction time of 4.5 h, the mixture is cooled to room temperature
filtrationthe suspension is filtered
customThe filtrate is freed of the solvent on a rotary evaporator
customdried under reduced pressure

Sources & evidence

ORD record: ord-293ea054bbcb41a2a6c27716753c2af0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388201B2

Reaction notes

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