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

Participants

Reaction Conditions

Reaction Steps

In a 500 ml four-necked flask having a reflux condenser, KPG stirrer, thermometer and gas inlet tube, 298 g of dry aniline were heated to 130° C. and 124 g of (chloromethyl)methyldimethoxysilane were added over the course of 60 min with stirring. After the end of the addition, ammonia was passed through the mixture with stirring at constant temperature until no further reaction was observable (about 60 min). Thereafter, excess aniline was removed under reduced pressure, the suspension was cooled to 30° C. and then 150 ml of isohexane were added. Thereafter, the white precipitate formed was filtered using a pressure filter, and was rinsed with two 80 ml portions of isohexane. Filtrate and wash solutions were combined and were freed from the solvent under reduced pressure. The subsequent fractional distillation gave 160 g (yield 95%) of (N-phenylaminomethyl)dimethoxy(methyl)silane having a chloride content of <20 ppm. When 1% of ammonia was added before the distillation of the product and any precipitate which had separated out was filtered off, a product having a chloride content of <10 ppm was obtained in the same yield.

Provenance & Evidence