Chloride → HCID 11547774, compound

HRID 1350592Notes

Reaction equation

HRID 1350592 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]([OH:14])[CH2:7][NH:8][C:9](=[O:13])[C:10]([CH3:12])=[CH2:11])[CH:2]=[CH2:3].[CH3:15][Si:16]([CH3:30])([CH3:29])[O:17][SiH:18]([O:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[O:19][Si:20]([CH3:23])([CH3:22])[CH3:21].[Cl-]>C1(C)C=CC=CC=1>[OH:14][CH:6]([CH2:5][O:4][CH2:1][CH2:2][CH2:3][Si:18]([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])([O:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[O:17][Si:16]([CH3:29])([CH3:30])[CH3:15])[CH2:7][NH:8][C:9](=[O:13])[C:10]([CH3:12])=[CH2:11]

Participants

5

Reactant 3

HCID 312ChlorideHCID 27608831873-89-8HCID 21097420HCID 21097420, compound

Product 1

HCID 11547774HCID 11547774, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
96 °C

Procedure

N-(3-Allyloxy-2-hydroxy-propyl)-2-methyl acrylamide made according to Example 9 (18 g, 0.09 mol), platinic chloride (4 mg, 100 ppm), BHT (36 mg, 2000 ppm) and toluene (90 mL) were charged into a 500 mL three-neck flask, equipped with a condenser with a nitrogen inlet and outlet, and a thermocouple connected to a temperature controller. Tris(trimethylsiloxy)silane (26.8 g, 0.09 mol) was added dropwise to the above mixture at 96–97° C. After stirred at about 96° C. for 16 hours, additional platonic chloride (4 mg, 100 ppm) was added to the reaction solution. The reaction was monitored by gas chromatography. After stirred for 47 hours, the reaction solution was washed with 0.5 N aqueous sodium hydroxide solution and twice with 2.5% aqueous sodium chloride solution. This was followed by washing with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulfate and filtered. The filtrate, inhibited with 4-methoxyphenol (0.02 g), was concentrated under reduced pressure at 30° C.–40° C. to give an oil (˜36 g). N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl)-2-methyl acrylamide was purified by column chromatography.

Workup

  1. additionwere charged into a 500 mL three-neck flask
  2. customequipped with a condenser with a nitrogen inlet and outlet
  3. stirringAfter stirred for 47 hours
  4. washthe reaction solution was washed with 0.5 N aqueous sodium hydroxide solution and twice with 2.5% aqueous sodium chloride solution
  5. washby washing with saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationwas concentrated under reduced pressure at 30° C.–40° C.

Sources & evidence

ORD record
ord-d2312a86a45c4f2f99a7dce08ee71b92
Source dataset
uspto-grants-2007_05
Patent number
US07214809B2

Reaction notes

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