Silylated derivatives OF N-(2-hydroxyphenyl)acetamide: Synthesis and structure

• The reaction of N-(2-(trimethylsilyloxy)phenyl)acetamide compound 1 with ClCH2SiMe2Cl in presence of triethylamine leads to formation of 4-acetyl-2,2-dimethyl-3,4-dihydro-2H-1,4,2-benzoxazasiline 3 represented as colorless crystals.
• An extreme broadening signal of methylene protons is exhibited in 1H NMR spectrum of this compound produced by rotation of acetyl moiety about CN bond.
• Structure of compound 1 and 3 were confirmed by X-ray data.

The N-(2-(trimethylsilyloxy)phenyl)acetamide 1 was synthesized via reaction of N-(2-hydroxyphenyl)acetamide with chlorotrimethylsilane. Transsilylation of new compound 1 by chloro(chloromethyl)dimethylsilane leads to 4-acetyl-2,2-dimethyl-3,4-dihydro-2H-1,4,2-benzoxazasiline 3. The structures of the new compounds were investigated by 1H, 13C and 29Si NMR spectroscopy, X-ray single-crystal analysis, FTIR spectroscopy and DFT methods.