Water → N-(3-(1,1,1,5,5,5-Hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)methacrylamide

HRID 373208Notes

Reaction equation

HRID 373208 reaction equation
[CH3:1][Si:2]([CH3:20])([CH3:19])[O:3][Si:4]([O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])([O:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH2:5][CH2:6][CH2:7][NH2:8].N1C=CC=CC=1.[C:27](Cl)(=[O:31])[C:28]([CH3:30])=[CH2:29].O>C(OCC)C>[CH3:11][Si:10]([CH3:13])([CH3:12])[O:9][Si:4]([CH2:5][CH2:6][CH2:7][NH:8][C:27](=[O:31])[C:28]([CH3:30])=[CH2:29])([O:3][Si:2]([CH3:19])([CH3:1])[CH3:20])[O:14][Si:15]([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 13528Methacryloyl chloride2×HCID 2756547(3-Aminopropyl)tris(trimethylsiloxy)silane

Product 1

HCID 16051444N-(3-(1,1,1,5,5,5-Hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)methacrylamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In 200 ml of ethyl ether was dissolved 36.6 g of the 3-[tris(trimethylsiloxy)silyl]propylamine obtained above, and the solution was added with 9.5 g of pyridine. The mixture was cooled in ice bath to 0°-5° C. Separately, 12.6 g of methacryloyl chloride was dissolved in 30 ml of ethyl ether. The methacryloyl chloride solution was placed in a separating funnel and dropped therefrom to the above mixture over about one hour. The mixture was continuously stirred for 16 hours. After the stirring, 200 ml of water was added to the reaction mixture, and the resulting mixture was stirred and the supernatant was separated. The supernatant was combined with the extract from the bottom layer with ethyl ether, and then ethyl ether was removed by heating. The residue was distilled in vacuo to give 36.6 g of a distillate at 165° C./2 mmHg.

Workup

  1. customobtained above, and the solution
  2. temperatureThe mixture was cooled in ice bath to 0°-5° C
  3. additiondropped
  4. stirringthe resulting mixture was stirred
  5. customthe supernatant was separated
  6. extractionextract from the bottom layer with ethyl ether
  7. customethyl ether was removed
  8. temperatureby heating
  9. distillationThe residue was distilled in vacuo
  10. customto give 36.6 g of a distillate at 165° C./2 mmHg

Sources & evidence

ORD record
ord-1b0edaf3d91c4a48b9db9f0155376c58
Source dataset
uspto-grants-1992_11
Patent number
US05162391

Reaction notes

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