Dimethylformamide → NSC265263

HRID 1657870Notes

Reaction equation

HRID 1657870 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][CH2:11][N:12]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][N:14]=[C:13]1[CH3:20])(=O)=O.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[N:1]([CH2:10][CH2:11][N:12]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][N:14]=[C:13]1[CH3:20])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 93141My 40.20

Product 1

HCID 3246588NSC265263

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 parts of sodium azide is added a solution of 32 parts of 2-(5-nitro-2-methyl-1-imidazolyl)ethyl methanesulfonate (Ger. Pat. No. 2,030,314) in 250 parts of warm N,N-dimethylformamide. The resultant mixture is stirred at approximately 50° for 6 hours, then diluted with 1000 parts of cold water. Sufficient potassium carbonate is added to insure basicity. The mixture thus obtained is extracted with toluene. The toluene extract is washed with water, dried over anhydrous potassium carbonate, and stripped of solvent by vacuum distillation, affording 1-(2-azidoethyl)-2-methyl-5-nitroimidazole as a yellow oil which is further purified by crystallization from ether. Isolated by filtration, washed with a 1:1 mixture of ether and hexane, and dried in air the purified product melts at 53°-54°. It has the formula ##SPC6##

Workup

  1. customThe mixture thus obtained
  2. extractionis extracted with toluene
  3. extractionThe toluene extract
  4. washis washed with water
  5. dry with materialdried over anhydrous potassium carbonate
  6. distillationstripped of solvent by vacuum distillation

Sources & evidence

ORD record
ord-c45319989cf84c249d0752ce9a50e2b3
Source dataset
uspto-grants-1976_06
Patent number
US03962274

Reaction notes

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