Date of Award
Union College Only
Bachelor of Science
N-Methyl-N-Phenylaminomethyltrimethylsilane (I) has been prepared by heating an ethereal solution of lithium N-Methyl-anilide and chloromethyltrimethylsilane in a sealed flask for two days at 110°. The peak ratios in the NMR spectrum of the product did not correspond to these expected for I but suggested a different product, N-Methyl-N-Trimethylsilylaniline (II). Elemental analysis favored II although it could also be interpreted to support I. The spectra of derivatives, and the substance’s stability to hydrochloric acid were characteristic of I. Tentative identification of ethylene as a by-product, and a small degree of reaction with hydrochloric acid support the presence of II, but only as an impurity. This hypothesis has been verified by gas chromatography, which showed the major product to be 94% pure and only one significant impurity present. The mass spectrum, however, showed no major peak at m/e 179, the molecular weight of 197 ± 2% determined by vapor phase osmometry provide convincing evidence in support of I. The methyl iodide and HCl salts of N-Methyl-N-Phenylaminomethyltrimethylsilane have been prepared and their identity confirmed by their NMR spectra.
Lichtenstein, Mark Stuart, "Synthesis of n-methyl-n-phenylaminomethyltrimethylsilane and n, n-dimethylanilinomethyltrimethylsilyl iodide" (1970). Honors Theses. 1800.