Ammonia → N-{[Dimethoxy(methyl)silyl]methyl}aniline

Participants

Reaction Conditions

Reaction Steps

In a 500 ml four-neck flask with reflux condenser, precision glass stirrer, thermometer and gas inlet tube, 298 g of dry aniline were heated to 130° C. and admixed with 124 g of (chloromethyl)methyl-dimethoxysilane with stirring within 60 min. When the addition had ended, ammonia was passed through the mixture with uniform temperature with stirring until no further reaction was observed (approx. 60 min). Thereafter, excess aniline was removed under reduced pressure, and the suspension was cooled to 30° C. and then admixed with 150 ml of isohexane. Subsequently, the white precipitate formed was filtered through a suction filter and washed with 2×80 ml of isohexane. Filtrate and wash solutions were combined and freed from the solvent under reduced pressure. The subsequent fractional distillation gave 160 g (95% yield) of (N-phenylaminomethyl)dimethoxy(methyl)silane with a chloride content of <20 ppm.

Provenance & Evidence