Water → 2-Methyl-1-(4-nitrobenzyl)-1H-imidazole

HRID 1721376Notes

Reaction equation

HRID 1721376 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.[N+:9]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1)([O-:11])=[O:10].O>CN(C=O)C.C(OCC)(=O)C>[CH3:3][C:4]1[N:5]([CH2:16][C:15]2[CH:18]=[CH:19][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)[CH:6]=[CH:7][N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromide

Product 1

HCID 50471292-Methyl-1-(4-nitrobenzyl)-1H-imidazoleYield 11.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (2.45 g, 61.0 mmol, 60% dispersion in oil) was added to a solution of 2-methylimidazole (5.0 g, 60.9 mmol) in DMF (100 ml). The mixture was stirred at room temperature for 0.25h before adding 4-nitrobenzyl bromide (13.2 g, 61.0 mmol) and heating at 110° C. for 2h followed by stirring at room temperture for 16h. Water (200 ml) and ethyl acetate (500 ml) were added, the aqueous separated and extracted with ethyl acetate (2×500 ml). The combined extracts were washed with water (3×250 ml), dried (MgSO4) and evaporated. The crude product was chromatographed on silica-gel eluting with CH2Cl2 /MeOH (96:4) to give the title-product (1.58 g); δ (360 MHz, CDCl3) 2.34 (3H, s, CH3), 5.16 (2H, s, CH2), 6.67 (1H, d, J=1.3 Hz, Ar--H), 7.03 (1H, d, J=1.3 Hz, Ar--H), 7.19 (2H, d, J=9.5Hz, Ar--H), 8.22 (2H, d, J=9.5Hz, Ar--H).

Workup

  1. customthe aqueous separated
  2. extractionextracted with ethyl acetate (2×500 ml)
  3. washThe combined extracts were washed with water (3×250 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was chromatographed on silica-gel
  7. washeluting with CH2Cl2 /MeOH (96:4)

Sources & evidence

ORD record
ord-9f2e330bad60432c93568fb1a1af23a4
Source dataset
uspto-grants-1996_04
Patent number
US05510362

Reaction notes

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