Pyrrolidine → Bis(pyrrolidinyl)methylvinylsilane

Over a 1.5 hour period, 145 grams (1.03 mol) of methylvinyldichlorosilane was added with stirring to a mixture under nitrogen at 0.C of 1 L of dry hexane and 293 grams (4.12 mols) of pyrrolidine. The resulting mixture was allowed to stir for about 12 hours while warming to room temperature. A solid white precipitate was filtered and washed with dry hexane under nitrogen. The solvent was removed under reduced pressure and the product was distilled giving 158 grams (73% yield) of bis(pyrrolidinyl)methylvinylsilane, having a boiling point of 50°-52° C. at less than 1 torr. There was added dropwise to 28.4 grams (135 millimoles) of bis(pyrrolidinyl) methylvinylsilane, which was stirring under nitrogen at 0° C., 26.7 grams (270 millimoles) of butylisocyanate. The reaction was stirred at 0° C. for a period of 12 hours. The mixture was then allowed to warm to room temperature over a 60 minute period. There was obtained a quantitative yield of bis(1,1-tetramethylene-3-butylureidomethylvinylsilane in the form of a clear viscous oil. Its identity was confirmed by IR and NMR. It is referred to hereinafter as the "bis(uriedo) coupler".

1. filtrationA solid white precipitate was filtered
2. washwashed with dry hexane under nitrogen
3. customThe solvent was removed under reduced pressure
4. distillationthe product was distilled

ORD-Eintrag

ord-e0fc841b911c40e89c828e05548159d2

Quelldatensatz

uspto-grants-1990_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04959407