Hydrogen Sulfide → HCID 131736106, compound

HRID 60569Notes

Reaction equation

HRID 60569 reaction equation
[SH2:1].[O-]CC.[Na+].[Si:6]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([NH:22][CH2:23][CH2:24]Cl)=[O:21])([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9]>C(O)C>[Si:6]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([NH:22][CH2:23][CH2:24][SH:1])=[O:21])([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 2723922Sodium ethoxideHCID 13362305N-(2-Chloroethyl)-N'-[3-(triethoxysilyl)propyl]urea

Product 1

HCID 131736106HCID 131736106, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of NaSH in ethanol [prepared by introducing H2S (15.21 g, 0.45 mol, 1.07 eq) into a sodium ethoxide solution (prepared from Na (10.55 g, 0.46 mol, 1.10 eq) in EtOH (300 mL))] is added, by metered addition at 52° C., (EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—Cl (138.90 g, 0.42 mol, 1.00 eq) in ethanol (300 ml), and the mixture is heated to 78° C. After a reaction time of 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—SH product (134.96 g, 97.9% of theory) is obtained as a white solid.

Workup

  1. additionis added, by metered addition at 52° C.
  2. filtrationthe suspension is filtered
  3. customThe filtrate is freed of the solvent on a rotary evaporator
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-286917f0d21946feaed1352c2befd518
Source dataset
uspto-grants-2016_09
Patent number
US09440998B2

Reaction notes

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