Sodium Sulfide → HCID 131736108, compound

HRID 1051975Notes

Reaction equation

HRID 1051975 reaction equation
[Si:1]([CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:17][CH2:18][CH2:19]Cl)=[O:16])([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[S-2:21].[Na+].[Na+]>C(O)C>[Si:1]([CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:17][CH2:18][CH2:19][S:21][CH2:19][CH2:18][NH:17][C:15]([NH:14][CH2:13][CH2:12][CH2:11][Si:1]([O:2][CH2:3][CH3:4])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10])=[O:16])=[O:16])([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 13362305N-(2-Chloroethyl)-N'-[3-(triethoxysilyl)propyl]urea

Product 1

HCID 131736108HCID 131736108, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a second reaction step, (EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—Cl (100.00 g, 0.31 mol, 2.00 eq) is initially charged in ethanol (75 ml) in a 500 ml three-neck flask with stirrer, reflux condenser and internal thermometer. Dry sodium sulphide (Na2S, 14.47 g, 0.18 mol, 1.17 eq) is added 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 (93.34 g, 99.2% of theory) is obtained as a waxy, light green solid.

Workup

  1. temperaturereflux condenser
  2. temperaturethe mixture is heated to reflux
  3. filtrationthe suspension is filtered
  4. customThe filtrate is freed of the solvent on a rotary evaporator
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-9af5bcb9418c45a18474ceb5b4840781
Source dataset
uspto-grants-2016_07
Patent number
US09388201B2

Reaction notes

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