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

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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.

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