Reaction #1745053

Reaction equation

sodium azide

2-(2-methyl-4-nitro-1-imidazolyl)ethyl methanesulfonate

→

1-(2-azidoethyl)-2-methyl-4-nitroimidazole

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Temperaturecooled
2. 2
   Otherpartitioned between water and toluene
3. 3
   OtherThe toluene phase is separated
4. 4
   Washwashed with water
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONstripped of solvent by vacuum distillation
7. 7
   OtherCrystallization of the residual oil
8. 8
   workup.ADDITIONfrom a mixture of ethyl acetate and hexane

Procedure

To 2 parts of sodium azide is added a solution of 5 parts of 2-(2-methyl-4-nitro-1-imidazolyl)ethyl methanesulfonate (U.S. Pat. No. 3,882,136) in 60 parts of N,N-dimethylformamide. The resultant mixture is stirred at approximately 55° for 4 hours, then cooled and thereupon partitioned between water and toluene. The toluene phase is separated, washed with water, dried over anhydrous magnesium sulfate, and stripped of solvent by vacuum distillation. Crystallization of the residual oil from a mixture of ethyl acetate and hexane affords 1-(2-azidoethyl)-2-methyl-4-nitroimidazole as colorless crystals melting at 73°-75°. The product has the formula ##SPC7##

Source