Methyl iodide → Methyl-tris(tris(trimethylsiloxy)silylpropyl)ammonium iodide

HRID 1478940Notes

Reaction equation

HRID 1478940 reaction equation
[CH3:1][Si:2]([CH3:58])([CH3:57])[O:3][Si:4]([CH2:15][CH2:16][CH2:17][N:18]([CH2:38][CH2:39][CH2:40][Si:41]([O:52][Si:53]([CH3:56])([CH3:55])[CH3:54])([O:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[O:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH2:19][CH2:20][CH2:21][Si:22]([O:33][Si:34]([CH3:37])([CH3:36])[CH3:35])([O:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[O:23][Si:24]([CH3:27])([CH3:26])[CH3:25])([O:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[O:5][Si:6]([CH3:9])([CH3:8])[CH3:7].C[I:60].[C:61](=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[I-:60].[CH3:61][N+:18]([CH2:38][CH2:39][CH2:40][Si:41]([O:52][Si:53]([CH3:55])([CH3:54])[CH3:56])([O:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[O:42][Si:43]([CH3:46])([CH3:45])[CH3:44])([CH2:17][CH2:16][CH2:15][Si:4]([O:5][Si:6]([CH3:7])([CH3:8])[CH3:9])([O:3][Si:2]([CH3:1])([CH3:57])[CH3:58])[O:10][Si:11]([CH3:12])([CH3:13])[CH3:14])[CH2:19][CH2:20][CH2:21][Si:22]([O:23][Si:24]([CH3:25])([CH3:26])[CH3:27])([O:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[O:28][Si:29]([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 86670505Tris(tris(trimethylsiloxy)silylpropyl)amine

Product 1

HCID 86670506Methyl-tris(tris(trimethylsiloxy)silylpropyl)ammonium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.42 g of tris(tris(trimethylsiloxy)silylpropyl)amine (30), 1.2 g of methyl iodide and 0.9 g of sodium carbonate are added to 50 ml of acetone. The reaction mixture is stirred for 15 hours at reflux. The solvent is evaporated and the residue taken up in methylene chloride. The organic phase is then washed with water, dried and evaporated. The residue contains the desired product methyl-tris(tris(trimethylsiloxy)silylpropyl)ammonium iodide (31); 1H-NMR (ppm, CDCl3): 3.27 6H t, 3.18 3H s, 1.56-1.50 6H m, 0.37 6H t, 0 81H s.

Workup

  1. temperatureat reflux
  2. customThe solvent is evaporated
  3. washThe organic phase is then washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-038ce83e3c734108ba1c4fddcd30246f
Source dataset
uspto-grants-2016_08
Patent number
US09403987B2

Reaction notes

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