Water → 4-methyl-1-(3-nitrophenyl)-1H-imidazole

HRID 484601Notes

Reaction equation

HRID 484601 reaction equation
F[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:11][C:12]1[N:13]=[CH:14][N:15]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 98231-Fluoro-3-nitrobenzeneHCID 11430Potassium CarbonateHCID 178418800HCID 178418800, compound

Product 1

HCID 150301664-methyl-1-(3-nitrophenyl)-1H-imidazoleYield 15.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 112.9 g of m-fluoronitrobenzene and 65.69 g of 4-methylimidazole in 1 liter of dimethylsulfoxide is added 58.51 g of potassium carbonate followed by heating under dry conditions at 110° C. for 39 hours. The reaction mixture is poured into 3.3 liters of water and stored in a refrigerator for 2 days. The mixture is filtered and the cake washed with copious volumes of water followed by suction drying to give 25 g of brown solid. The solid is crystallized from ethyl acetate to give 15.0 g of the desired product as a beige solid, m.p. 119°-120° C. From the combined recrystallization filtrates is obtained 800 mg of 5-methyl-1-(3-nitrophenyl)-1H-imidazole as a beige solid, m.p. 130°-132° C.

Workup

  1. filtrationThe mixture is filtered
  2. washthe cake washed with copious volumes of water
  3. customdrying

Sources & evidence

ORD record
ord-8a74b69f77e94ea481b6abdb1d364db1
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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