Water → 1-methyl-2-[(2-nitrophenoxy)methyl]-1H-imidazole

HRID 983355Notes

Reaction equation

HRID 983355 reaction equation
[Na].[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([O-:4])=[O:3].C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH3:19][N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25]Cl.O>CN(C)C=O>[CH3:19][N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[N+:2]([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27954062-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 569236172-Nitrophenol, sodium salt

Product 1

HCID 225596511-methyl-2-[(2-nitrophenoxy)methyl]-1H-imidazoleYield 41.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.92 g (11.97 mmol) of o-nitrophenol sodium salt, 3.8 g (35.9 mmol) of sodium carbonate, 2 g (11.97 mmol) of 1-methyl-2-chloromethylimidazole hydrochloride in 30 ml of N,N-dimethylformamide were heated at 50° C. for 2 hours. The mixture was then poured into water and extracted with ethylacetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated, affording 1.17 g of the title compound, recrystallized from diethylether.

Workup

  1. extractionextracted with ethylacetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-f0e12bf4cf334c17b16f95dd37920f4c
Source dataset
uspto-grants-2005_03
Patent number
US06863647B2

Reaction notes

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