Methyl Methanesulfonate → Trimethoxysilylpropyltrimethylammonium methanesulfonate

HRID 537716Notes

Reaction equation

HRID 537716 reaction equation
[CH3:1][O:2][Si:3]([CH2:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])([O:6][CH3:7])[O:4][CH3:5].[CH3:14][S:15]([O:18]C)(=[O:17])=[O:16]>C(OCC)(=O)C>[CH3:14][S:15]([O-:18])(=[O:17])=[O:16].[CH3:1][O:2][Si:3]([CH2:8][CH2:9][CH2:10][N+:11]([CH3:14])([CH3:13])[CH3:12])([O:4][CH3:5])[O:6][CH3:7]

Participants

4

Reactant 2

HCID 4156Methyl MethanesulfonateHCID 756681-Propanamine, N,N-dimethyl-3-(trimethoxysilyl)-

Product 1

HCID 86654371Trimethoxysilylpropyltrimethylammonium methanesulfonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

5.0 g of trimethoxysilylpropyldimethylamine and 18 g of ethyl acetate were charged into a 100 mL flask to be dissolved. While stirring the resultant mixed solution with a magnetic stirrer, to the mixed solution, a solution in which 4.0 g of methyl methanesulfonate was dissolved in 24 g of ethyl acetate was gradually added at room temperature in a nitrogen atmosphere. The reaction mixture was refluxed over 3 days and therefrom, ethyl acetate was distilled off under reduced pressure. The resultant concentrate was dropped into 100 mL of diethyl ether and therefrom, trimethoxysilylpropyldimethylamine and methyl methanesulfonate as by-products were removed. This purification was repeated three times and then remaining diethyl ether was distilled off under reduced pressure, followed by dissolving the resultant concentrate in methanol to obtain a 30% methanol solution of trimethoxysilylpropyltrimethylammonium methanesulfonate.

Workup

  1. dissolutionto be dissolved
  2. additionmixed solution with a magnetic stirrer
  3. additionwas gradually added at room temperature in a nitrogen atmosphere
  4. temperatureThe reaction mixture was refluxed over 3 days
  5. distillationethyl acetate was distilled off under reduced pressure
  6. concentrationThe resultant concentrate
  7. additionwas dropped into 100 mL of diethyl ether
  8. customtrimethoxysilylpropyldimethylamine and methyl methanesulfonate as by-products were removed
  9. customThis purification
  10. distillationremaining diethyl ether was distilled off under reduced pressure
  11. dissolutionby dissolving the resultant
  12. concentrationconcentrate in methanol

Sources & evidence

ORD record
ord-b4986cc230cf40e2be1af5612bdfc87e
Source dataset
uspto-grants-2014_10
Patent number
US08864894B2

Reaction notes

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