Ethylazidoformate synthesis

4synthesis methods

Product Name:Ethylazidoformate
CAS Number:817-87-8
Molecular formula:C3H5N3O2
Molecular Weight:115.0907

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Yield: 80%

Reaction Conditions:

with sodium azide in diethyl ether;water at 20;Cooling with ice;

Steps:

General procedure: Sodium azide (157 mmol) was dissovled in 55 mL of H2O and cooled in an icebath. Ethyl chloroformate (131 mmol) in 15 mL of diethyl ether was thenadded to the aqueous sodium azide. The reaction was stirred vigorouslyovernight, warming to room temperature. The reaction was extracted intodiethyl ether (2 40 mL) and the organics were dried over MgSO4 andconcentrated under reduced pressure. EAF was isolated as a transparent oil in80% yield. CAUTION: ethyl azidoformate can decompose explosively attemperatures above 160 C.

References:

McLaughlin, Emily C.;Shrestha, Anuska;Fletcher, Madison H.;Steinauer, Nathaniel S.;Shinn, Min Kyung;Shahid, Sabrina M. [Tetrahedron Letters,2013,vol. 54,# 40,p. 5461 - 5463]

623-33-6 Synthesis