Sodium Azide → HCID 21530700, compound

HRID 1657871Notes

Reaction equation

HRID 1657871 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[N:14]=[C:13]1[CH3:20])(=O)=O>CN(C)C=O>[N:1]([CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[N:14]=[C:13]1[CH3:20])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 21530699HCID 21530699, compound

Product 1

HCID 21530700HCID 21530700, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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##

Workup

  1. temperaturecooled
  2. custompartitioned between water and toluene
  3. customThe toluene phase is separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationstripped of solvent by vacuum distillation
  7. customCrystallization of the residual oil
  8. additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-3802be5709d94e878275f50d588faf92
Source dataset
uspto-grants-1976_06
Patent number
US03962274

Reaction notes

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