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

HRID 26469

Reaction equation

HRID 26469 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[N-:7]=[N+:8]=[N-:9].[Na+]>C1C=CC=CC=1.Cl>[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]=[N+:8]=[N-:9])=[O:6]

Participants

5

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 33557Sodium Azide

Product 1

HCID 13481262(2-Chloroethyl)carbamyl azideYield 88%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. customThe two-phase reaction mixture
  2. customthe water phase was removed
  3. custom2-chloroethylcarbamoyl azide was crystallized from benzene/petroleum ether in the form of white needles

Sources & evidence

ORD record
ord-a0178d1904114babb7649513b46595b2
Source dataset
uspto-grants-1979_04
Patent number
US04150146

Linked notes

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