2-Chloroethyl isocyanate → (2-Chloroethyl)carbamyl azide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloroethyl isocyanate (0.2 mole) in 100 ml of benzene was slowly added to a stirred solution of activated sodium azide (0.2 mole) in 100 ml of hydrochloric acid (13%) maintained at 0° C. The two-phase reaction mixture was stirred for 4 hours at 0° C. and the water phase was removed. 2-chloroethylcarbamoyl azide was crystallized from benzene/petroleum ether in the form of white needles. Yield: 88%. M.P. 49.6 to 50.2° C. NMR(CDCl3 -TMS)δ=3.4 to 3.9 ppm (unres., 4H, CH2 --CH2Cl); 6.12 ppm (br, s, iH, NH); MS(14 v):m/e 148(M+), m/e 106(M--N3)+, m/e 105 (M--HN3)+=base peak. An intensity ratio of m/e 148 / m/e 150 is typical for a monochlorinated compound.

Provenance & Evidence