N-Methylacetamide → Acetamide, N-[(1,1-dimethylethyl)dimethylsilyl]-N-methyl-

To a vigorously stirred solution of 73.1 g (1.0 mole) N-methylacetamide dissolved in 1400 ml of dry triethylamine was added 196 g (1.30 mole) of t-butyldimethylsilyl chloride. The flask was purged with dry nitrogen and then equipped with a drying tube. Hard stirring of the mixture was continued for 24 hours at room temperature. Then, under a layer of dry air, the reaction mixture was filtered to remove the precipitate of triethylamine hydrochloride. The resulting filter cake was then washed three times with 150 ml each of dry triethylamine. The filtrate and washings were combined and reduced in volume by distillation at 35 degrees C. at 10 mm Hg. The remaining straw colored liquid was then fractionally distilled.

1. customThe flask was purged with dry nitrogen
2. customequipped with a drying tube
3. filtrationThen, under a layer of dry air, the reaction mixture was filtered
4. customto remove the precipitate of triethylamine hydrochloride
5. filtrationThe resulting filter cake
6. washwas then washed three times with 150 ml each of dry triethylamine
7. distillationreduced in volume by distillation at 35 degrees C
8. distillationThe remaining straw colored liquid was then fractionally distilled

ORD record

ord-1c276bbd84fa47f2acd7581ae16d3d0f

Source dataset

uspto-grants-1984_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04467037