Dimethyl Sulfate → Imidazole, 1,2,4-trimethyl-5-nitro-

HRID 2118540Notes

Reaction equation

HRID 2118540 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([N+:8]([O-:10])=[O:9])=[C:5]([CH3:7])[N:6]=1.[CH3:11]OS(OC)(=O)=O.C(=O)(O)[O-].[Na+]>O>[CH3:11][N:3]1[C:4]([N+:8]([O-:10])=[O:9])=[C:5]([CH3:7])[N:6]=[C:2]1[CH3:1]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 1355544302,4-Dimethyl-5-nitro-1H-imidazole (9CI)

Product 1

HCID 146466Imidazole, 1,2,4-trimethyl-5-nitro-Yield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,4-dimethyl-5-nitroimidazole (7.0 g, 0.05 mole) and dimethylsulfate (7.0 ml, 0.074 mole) were heated at 100° C. for 1 hour 50 minutes. After cooling to room temperature, the reaction mixture was added to about 60 ml of water. Solid sodium bicarbonate was added until the solution is basic, and the mixture was then cooled on ice. The resulting crystals were filtered off and dried to give 6.2 g. This was recrystallized from water to give 4.5 g of 1,2,4-trimethyl-5-nitroimidazole.

Workup

  1. temperaturethe mixture was then cooled on ice
  2. filtrationThe resulting crystals were filtered off
  3. customdried
  4. customto give 6.2 g
  5. customThis was recrystallized from water

Sources & evidence

ORD record
ord-cfa53942332b4d0795d58f53d70c3ebe
Source dataset
uspto-grants-1987_07
Patent number
US04678799

Reaction notes

Loading…