Potassium Chloride → 5,5-dimethyl-3-trimethoxysilylpropyl Hydantoin

HRID 648371Notes

Reaction equation

HRID 648371 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[OH-].[K+].Cl[CH2:13][CH2:14][CH2:15][Si:16]([O:21][CH3:22])([O:19][CH3:20])[O:17][CH3:18].[Cl-].[K+].[SiH4]>CN(C)C=O.C(O)C>[CH3:1][C:2]1([CH3:9])[N:6]([CH2:13][CH2:14][CH2:15][Si:16]([O:21][CH3:22])([O:19][CH3:20])[O:17][CH3:18])[C:5](=[O:7])[NH:4][C:3]1=[O:8]

Participants

8

Reactant 5

HCID 4873Potassium ChlorideHCID 6491DimethylhydantoinHCID 14797Potassium HydroxideHCID 23953SilaneHCID 624493-(Trimethoxysilyl)propyl chloride2×

Product 1

HCID 222748335,5-dimethyl-3-trimethoxysilylpropyl Hydantoin

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture containing 12.8 g (0.1 mole) 5,5-dimethylhydantoin, 5.6 g (0.1 mole) potassium hydroxide and 100 cc ethanol was heated to the boiling point until a clear solution was obtained. The ethanol was then evaporated under reduced pressure to isolate the solid, anhydrous salt. The salt was combined with 100 cc of dry N,N-dimethylformamide and the resultant mixture was heated at 50° C. until a clear solution formed. A 19.8 g (0.1 mole) portion of chloropropyl trimethoxysilane was then added dropwise to the aforementioned salt solution under a nitrogen atmosphere with stirring. The temperature of the reaction mixture increased slightly during the addition, which is indicative of an exothermic reaction, and a white precipitate (potassium chloride) began to form when the silane addition was begun. Following completion of the addition the reaction mixture was heated at 95° C. for three hours. Analysis by vapor phase chromatography of the liquid phase demonstrated that the initial chloropropyl trimethoxysilane had been converted to a product exhibiting a high retention time. The reaction mixture was then cooled and filtered, following which the liquid phase was distilled to remove the N,N-dimethylformamide. A second fraction was collected at a temperature of 194° C. and a pressure of 4 mm of mercury and subsequently solidified to a white solid. Analysis by vapor phase chromatography indicated that this material was 98% pure and contained a trace amount of the initial hydantoin. The infra-red spectrum of the material was consistent with the proposed structure ##STR7## The product was found to contain 9.74% by weight of silicon and 9.92% nitrogen. The calculated values for the expected product are 9.64% silicon and 9.66% nitrogen.

Workup

  1. temperaturewas heated to the boiling point until a clear solution
  2. customwas obtained
  3. customThe ethanol was then evaporated under reduced pressure
  4. customto isolate the solid, anhydrous salt
  5. customformed
  6. temperatureThe temperature of the reaction mixture increased slightly during the addition, which
  7. customis indicative of an exothermic reaction
  8. customto form when
  9. additioncompletion of the addition the reaction mixture
  10. temperatureThe reaction mixture was then cooled
  11. filtrationfiltered
  12. distillationwas distilled
  13. customto remove the N,N-dimethylformamide
  14. customA second fraction was collected at a temperature of 194° C.

Sources & evidence

ORD record
ord-0e343630d9fb46f48519006713a78e54
Source dataset
uspto-grants-1983_10
Patent number
US04412078

Reaction notes

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