Water → 1,2-Dimethyl-4-nitro-1H-imidazole

HRID 1022255Notes

Reaction equation

HRID 1022255 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[C:10]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[CH3:10][N:3]1[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]1[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178433402HCID 178433402, compound

Product 1

HCID 257911,2-Dimethyl-4-nitro-1H-imidazoleYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-methyl-4-nitro-1H-imidazole (10.0 g, 78.7 mmol) and K2CO3 (21.7 g, 160 mmol) in DMF (80 mL) was added CH3I (13.4 g, 94 mmol) dropwise while stirring at room temperature. The mixture was stirred for 2 h. Water (200 mL) was then added to the mixture. The resulting suspension was filtered, washed with water, and dried in vacuo to afford 337a as a white solid (5.0 g, 45%). MS-ESI: [M+H]+ 142.1.

Workup

  1. stirringThe mixture was stirred for 2 h
  2. filtrationThe resulting suspension was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bcb264708d1944c0b0b10beb1a50e837
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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