Water → HCID 21644775, compound

HRID 373209Notes

Reaction equation

HRID 373209 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][Si:6]([O:17][Si:18]([CH3:21])([CH3:20])[CH3:19])([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[O:7][Si:8]([CH3:11])([CH3:10])[CH3:9].N1C=CC=CC=1.[C:28](Cl)(=[O:32])[C:29]([CH3:31])=[CH2:30].O>C(OCC)C>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][Si:6]([O:7][Si:8]([CH3:9])([CH3:10])[CH3:11])([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[O:17][Si:18]([CH3:19])([CH3:21])[CH3:20])[C:28](=[O:32])[C:29]([CH3:31])=[CH2:30]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 13528Methacryloyl chloride2×HCID 155196903-{1,1,1,5,5,5-Hexamethyl-3-[(trimethylsilyl)oxy]trisiloxan-3-yl}-N-methylpropan-1-amine

Product 1

HCID 21644775HCID 21644775, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In 200 ml of ethyl ether was dissolved 32.6 g of the N-methyl-3-[tris(trimethylsiloxy)silyl]propylamine obtained above, and the solution was added with 11 g of pyridine. The mixture was cooled in ice bath to 0°-5° C. Separately, 14.5 g of methacryloyl chloride was dissolved in 45 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 then 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 33.0 g of a distillate at 155° C./3 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. customsupernatant 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 33.0 g of a distillate at 155° C./3 mmHg

Sources & evidence

ORD record
ord-f3755257beb242b2af852e70b5e1fe43
Source dataset
uspto-grants-1992_11
Patent number
US05162391

Reaction notes

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