Chlorotrimethylsilane → N-methyl-N-trimethylsilylacrylamide

참여 물질

반응 단계

N-methylacrylamide (50.9 g, 0.6 mole) and triethylamine (67 g, 0.67 mole) were added to 300 mL of acetonitrile in a 500 mL round-bottomed flask. The reaction vessel was fitted with a reflux condenser topped with a rubber stopper that contained two needles, one connected to a source of nitrogen gas and other to an oil bubbler. A solution of trimethylsilyl chloride (72.4 g, 0.67 mole) in a 50 mL acetonitrile was added dropwise to this mixture. A white precipitate formed almost immediately. The amount of precipitate continued to increase throughout the addition and the color of the solution changed from colorless to orange. After the addition was completed, the resulting slurry was allowed to stir at room temperature for six hours. The mixture was filtered using vacuum filtration in a dry bag filled with nitrogen. The white precipitate was collected as a filter cake. NMR-T60 analysis indicated the filter cake was the triethylammonium chloride, the expected by-product. The orange colored filtrate concentrated in vacuo gave a dark red material. The crude mixture was subjected to vacuum fractional distillation. The first fraction distilled at 22°-35° C. at 0.3 mm Hg. NMR analysis showed it was mostly acetonitrile and a small amount of product. The second fraction distilled at 35°-45° C. at 0.3 mm Hg and appeared to be the desired pure product on NMR analysis. The third fraction distilled at 70°-80° C. at 0.3 mm Hg. NMR analysis showed it was N-methyl acrylamide. The pot contained uncharacterized polymerized material as a black viscous material. The reaction gave about 45% yield.

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