Water → HCID 21107845, compound

HRID 2116804Notes

Reaction equation

HRID 2116804 reaction equation
[C:1]([CH2:3][C:4](Cl)=[O:5])#[N:2].[CH3:7][Si:8]([CH2:19][CH2:20][CH2:21][NH2:22])([O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[O:9][Si:10]([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C.O>ClCCl>[C:1]([CH2:3][C:4]([NH:22][CH2:21][CH2:20][CH2:19][Si:8]([CH3:7])([O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[O:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 109128993-(3-Aminopropyl)heptamethyltrisiloxaneHCID 110515942-Cyanoacetyl chloride

Product 1

HCID 21107845HCID 21107845, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanoacetyl chloride (5.2 g, 0.05 mol) is added dropwise over 20 minutes to a mixture of 3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propylamine (13.93 g, 0.05 mol) and of triethylamine (5 g, 0.05 mol) in 40 ml of dichloromethane. The temperature rises to 32° C. The mixture is refluxed for two hours. The reaction mixture is poured into 150 ml of water and is extracted with dichloromethane. The organic phases are washed with water and dried over sodium sulfate, and the solvent is then evaporated off. After purification by passing through a column of silica (eluent: 70/30 heptane/ethyl acetate), 12.2 g (70% yield) of cyano-N-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]acetamide are obtained in the form of a colorless oil, which is used without further purification in the following step.

Workup

  1. customrises to 32° C
  2. temperatureThe mixture is refluxed for two hours
  3. extractionis extracted with dichloromethane
  4. washThe organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is then evaporated off
  7. customAfter purification

Sources & evidence

ORD record
ord-3e13371d10094e938344fb47f79d8d8e
Source dataset
uspto-grants-2008_10
Patent number
US07439380B2

Reaction notes

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