N,N'-Diphenyl-P-Phenylenediamine → 3-(Trimethoxysilyl)propyl methacrylate

HRID 1197198Notes

Reaction equation

HRID 1197198 reaction equation
[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[K+].C1C=CC(NC2C=CC(NC3C=CC=CC=3)=CC=2)=CC=1.Cl[CH2:29][CH2:30][CH2:31][Si:32]([O:37][CH3:38])([O:35][CH3:36])[O:33][CH3:34]>CN(C)C1C=CN=CC=1>[C:1]([O:6][CH2:29][CH2:30][CH2:31][Si:32]([O:37][CH3:38])([O:35][CH3:36])[O:33][CH3:34])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 6319N,N'-Diphenyl-P-PhenylenediamineHCID 624493-(Trimethoxysilyl)propyl chlorideHCID 23667354Potassium methacrylate

Product 1

HCID 173183-(Trimethoxysilyl)propyl methacrylateYield 92%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
135 °C

Procedure

1.74 g (0.015 mol) of 4-dimethylaminopyridine were dissolved in 201.5 (1.015 mol) of 3-chloropropyltrimethoxysilane, and the solution was heated to 135° C. while stirring, and was maintained at this temperature for 15 minutes. After the solution had been cooled to 60° C., 124.2 g (1 mol) of potassium methacrylate and 0.6 g of N,N'-diphenyl-p-phenylenediamine were added. The mixture was then heated to 135° C. again and maintained at that temperature for 1 hour. Thereafter, it was cooled, and the potassium chloride which had precipitated was filtered off and washed with 80 g of methanol. The methanol was evaporated from the combined filtrates, and the residue was distilled under reduced pressure. 228.1 g of 3- methacryloxypropyltrimethoxysilane having a boiling point of 83° C. (0.4 mbar) were obtained. The yield was 92% of theory, based on the amount of potassium methacrylate used. The purity of the end product was 99.0%. In the gas chromatogram only traces of 4-dimethylaminopyridine were detectable.

Workup

  1. temperaturewas maintained at this temperature for 15 minutes
  2. temperatureAfter the solution had been cooled to 60° C.
  3. temperatureThe mixture was then heated to 135° C. again
  4. temperaturemaintained at that temperature for 1 hour
  5. temperatureThereafter, it was cooled
  6. customthe potassium chloride which had precipitated
  7. filtrationwas filtered off
  8. washwashed with 80 g of methanol
  9. customThe methanol was evaporated from the combined filtrates
  10. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-79731f135ecc486e81da714f75db9a1a
Source dataset
uspto-grants-1992_05
Patent number
US05117027

Reaction notes

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