N-(2-Chloroethyl)-N'-[3-(triethoxysilyl)propyl]urea → HCID 58903422, compound

HRID 1051972Notes

Reaction equation

HRID 1051972 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].[C:21]([O-])(=[S:23])C.[K+]>C(O)C>[Si:1]([CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:17][CH2:18][CH2:19][S:23][CH3:21])=[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 13362305N-(2-Chloroethyl)-N'-[3-(triethoxysilyl)propyl]ureaHCID 23670855Potassium ethanethioate

Product 1

HCID 58903422HCID 58903422, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—Cl (81.52 g, 0.25 mol, 1.00 eq) is initially charged in ethanol (85 ml) in a 500 ml three-neck flask with stirrer, reflux condenser and internal thermometer. Potassium thioacetate (28.48 g, 0.25 mol, 1.00 eq) is added and the mixture is heated to reflux. After a reaction time of 3.5 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—CH3 product (81.64 g, 89% of theory) is obtained as a light brown 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-0926083c03994e91ac0877b72ed94372
Source dataset
uspto-grants-2016_07
Patent number
US09388200B2

Reaction notes

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