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

HRID 484604Notes

Reaction equation

HRID 484604 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C:12]1[NH:13][CH:14]=[CH:15][N:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:11][C:12]1[N:13]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:14]=[CH:15][N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 127492-Methylimidazole

Product 1

HCID 100131182-Methyl-1-(4-nitrophenyl)-1H-imidazoleYield 112.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 50.0 g of p-fluoronitrobenzene, 85.93 g of 2-methylimidazole and 44.9 g of potassium carbonate in 860 ml of dimethylsulfoxide is heated at 120° C. for 24 hours. The mixture is poured into 2.5 liter of water and stored in a refrigerator for two days. The mixture is filtered and cake washed with copious volumes of water and vacuum dried. The cake is dissolved in 1500 ml of ethyl acetate, filtered through hydrous magnesium silicate and the filtrate reduced to about 500 ml, cooled and the resulting solid, filtered, and air dried to give 81.0 g of the desired product as brown crystals, m.p. 135°-137° C.

Workup

  1. filtrationThe mixture is filtered
  2. washcake washed with copious volumes of water and vacuum
  3. customdried
  4. dissolutionThe cake is dissolved in 1500 ml of ethyl acetate
  5. filtrationfiltered through hydrous magnesium silicate
  6. temperaturecooled
  7. filtrationthe resulting solid, filtered
  8. customair dried

Sources & evidence

ORD record
ord-e4b0bba98c244359be9c682e04a2bf7a
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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