Acetonitrile → Acetic acid, azido-, ethyl ester

To a solution of 490 g. (4 moles) of ethyl chloroacetate in 1500 ml. of acetonitrile were added 260 g. (4 moles) of sodium azide, and the mixture was heated at the reflux temperature for 20 hours. After heating, the reaction mixture was poured into 1 liter of water with stirring for 1/2 hour. The organic phase was separated from the aqueous phase and evaporated in vacuo to dryness. The yellow residual oil was dissolved in 1200 ml. of diethyl ether and the solution was dried over magnesium sulfate. Evaporation of the diethyl ether in vacuo gave 391 g. (76% yield) of ethyl azidoacetate.

1. temperatureAfter heating
2. customThe organic phase was separated from the aqueous phase
3. customevaporated in vacuo to dryness
4. dissolutionThe yellow residual oil was dissolved in 1200 ml
5. dry with materialof diethyl ether and the solution was dried over magnesium sulfate
6. customEvaporation of the diethyl ether in vacuo
7. customgave 391 g

ORD record

ord-3f6ecd852a4444bdab98d2e69e2ba745

Source dataset

uspto-grants-1981_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04304774