Methyl Acetate → N-Benzylacetamide

2.1 g. of benzylamine, 7.4 g. of methyl acetate and 1.5 g. of the sodium salt of 4,6-dimethyl-2-hydroxypyridine are dissolved in 30 ml. of dimethyl acetamide and heated at about 78° C. for 4.5 hours. As determined by thin layer chromatography, all but a trace of the benzylamine is consumed. 200 ml. of water and 0.9 ml. of concentrated hydrochloric acid are added to the reaction solution, and the solution is extracted three times with 100 ml. of ethyl acetate. The organic layer is washed with 100 ml. of water, and, after drying with sodium sulfate, concentrated and crystallized. Recrystallization from 300 ml. of ether-petroleum benzin (1:1), 2.5 g. of needle-like crystals of N-benzyl acetamide are obtained (yield: 84 percent). m.p. 60.5° - 62° C.

1. customall but a trace of the benzylamine is consumed
2. additionof concentrated hydrochloric acid are added to the reaction solution
3. extractionthe solution is extracted three times with 100 ml
4. washThe organic layer is washed with 100 ml
5. dry with materialof water, and, after drying with sodium sulfate
6. concentrationconcentrated
7. customcrystallized
8. customRecrystallization from 300 ml

ORD record

ord-09504f88b94f4fe5a9214a23cf77d119

Source dataset

uspto-grants-1977_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE029369