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

HRID 2399716Notes

Reaction equation

HRID 2399716 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>[N+:9]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:5]2[CH:6]=[CH:7][N:8]=[C:4]2[CH3:3])=[CH:14][CH:13]=1)([O-:11])=[O:10]

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 0.25 h before adding 4-nitrobenzyl bromide (13.2 g, 61.0 mmol) and heating at 110° C. for 2 h followed by stirring at room temperature for 16 h. 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 (4%) to give the title-product (1.58 g, 10.5%); δ (360 MHz, CDCl3) 2.34 (3H, s, Me); 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=9.5 Hz, Ar--H); 8.22 (2H, d, J=9.5 Hz, Ar--H).

Workup

  1. temperatureheating at 110° C. for 2 h
  2. stirringby stirring at room temperature for 16 h
  3. customthe aqueous separated
  4. extractionextracted with ethyl acetate (2×500 ml)
  5. washThe combined extracts were washed with water (3×250 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude product was chromatographed on silica gel eluting with CH2Cl2 /MeOH (4%)

Sources & evidence

ORD record
ord-654925a4d00b47518a66a79b6111077c
Source dataset
uspto-grants-1995_09
Patent number
US05451588

Reaction notes

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