7449-74-3

clear light yellow liquid

The interaction of N-Methyl-N-(trimethylsilyl)acetamide with chloromethyl(methyl)-diacetoxysilane led to the formation of 2,4,6-trimethyl-2,4-bis((N-methylacetamido)methyl)-1,3,5,2,4-trioxadisilinan-6-ylium chloride[1].

reagent type: derivatization reagent
reaction type: Silylations

N-Methyl-N-trimethylsilylacetamide [7449-74-3] M 145.3, b 48 -49o/11mm, 8 4o/13mm, 105-107o/35mm (solid at room temperature), d 4 0.90, n D 1.4379. A likely impurity is Et3N.HCl which can be detected by its odour. If it is completely soluble in *C6H6, then redistil; otherwise dissolve it in this solvent, filter and evaporate first in a vacuum at 12mm, then fractionate; all operations should be carried out in a dry N2 atmosphere. [Klebe et al. J Am Chem Soc 88 3390 1966, Ried & Suarez-Rivero Chem Ber 96 1473 1963, Beilstein 4 IV 4011.]

[1] Nataliya F. Lazareva, Igor M.Lazarev,lrina V.Sterkhova. "Trans-silylationof N-methyl-N-trimethylsilylacetamide with chloromethyl(methyl)diacetoxysilane."Journal of Organometallic Chemistry1006 (2023): Article 123000.