Pyridine → HCID 67233482, compound

HRID 537706Notes

Reaction equation

HRID 537706 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:7][O:8][Si:9]([CH2:14][CH2:15][CH2:16][Cl:17])([O:12][CH3:13])[O:10][CH3:11]>C(OCC)(=O)C>[Cl-:17].[CH3:7][O:8][Si:9]([CH2:14][CH2:15][CH2:16][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O:12][CH3:13])[O:10][CH3:11]

Participants

4

Reactant 2

HCID 1049PyridineHCID 624493-(Trimethoxysilyl)propyl chloride

Product 1

HCID 67233482HCID 67233482, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3.0 g of pyridine 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 11.3 g of trimethoxysilylpropyl chloride 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, pyridine and trimethoxysilylpropyl chloride 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 trimethoxysilylpropylpyridinium chloride.

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. custompyridine and trimethoxysilylpropyl chloride 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-aa3b0dd146bc47ea9920d16392d19f08
Source dataset
uspto-grants-2014_10
Patent number
US08864894B2

Reaction notes

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