Triethoxy(3-isocyanatopropyl)silane → HCID 131736107, compound

HRID 1051974Notes

Reaction equation

Cl.Cl[CH2:3][CH2:4][NH2:5].[O-]CC.[Na+].[N:10]([CH2:13][CH2:14][CH2:15][Si:16]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[C:11]=[O:12].[C:26]([O-])(=[S:28])[CH3:27].[K+]>C(O)C>[Si:16]([CH2:15][CH2:14][CH2:13][NH:10][C:11]([NH:5][CH2:4][CH2:3][S:28][CH2:26][CH3:27])=[O:12])([O:23][CH2:24][CH3:25])([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: -78 °C

Procedure

2-Chloroethylamine hydrochloride (73.86 g, 0.70 mol, 1.00 eq) is initially charged in ethanol (2.0 l) in a 4 l three-neck flask with precision glass stirrer, internal thermometer, dropping funnel and reflux condenser, and cooled to −78° C., and sodium ethoxide (226.83 g, 0.70 mol, 1.00 eq, 21% in ethanol) is added. 3-Isocyanatopropyl(triethoxysilane) (173.15 g, 0.70 mol, 1.00 eq) is then added dropwise at −78 to −65° C. within 3 h and then the mixture is heated to 50° C. Potassium thioacetate (79.95 g, 0.70 mol, 1.00 eq) is added in five portions and the mixture is heated to reflux. After a reaction time of 4 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—CH2CH3 product (288.02 g, quant.) is obtained as an orange oil.

Workup

temperaturereflux condenser
temperaturethe mixture is heated to 50° C
temperaturethe mixture is heated to reflux
temperatureAfter a reaction time of 4 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-7e64248970844186bafb5c68f75d55ff
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388200B2

Reaction notes

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