Water → 4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole

HRID 475706Notes

Reaction equation

HRID 475706 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[O:17][CH3:18].[OH-].[K+].O>CS(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[O:17][CH3:18])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisoleHCID 178478287HCID 178478287, compound

Product 1

HCID 580753854-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazoleYield 42%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-1H-imidazole (5.0 g, 48.8 mmol), 1-chloro-2-methoxy-4-nitrobenzene (9.15 g, 48.8 mmol), and potassium hydroxide flakes (2.74 g, 48.8 mmol) in anhydrous DMSO (50 mL) was heated at 80° C. for 20 h. The reaction mixture was allowed to cool to rt and was poured into 800 mL of water with vigorous stirring. The resulting yellow-orange precipitate was collected by vacuum filtration using a coarse sintered glass funnel. The crude wet solid was transferred to a 1 L Erlenmeyer flask. Absolute ethanol (250 mL) was added to the flask and the resulting suspension was heated until all of the solids dissolved. The clear solution was cooled to rt and the desired product slowly crystallized. After 2 h, the crystalline solid was collected by vacuum filtration and rinsed with 100 mL of fresh ethanol. The solid was dried under high vacuum to afford 4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole (5.2 g, 42% yield) as an off-white crystalline solid. LC-MS (M+H)+=254.0. 1H NMR (500 MHz, CDCl3) δ ppm 7.94-8.01 (m, 2H) 7.76 (d, J=1.53 Hz, 1H) 7.45 (d, J=8.55 Hz, 1H) 7.21 (d, J=1.53 Hz, 1H) 4.02 (s, 3H).

Workup

  1. temperatureto cool to rt
  2. filtrationThe resulting yellow-orange precipitate was collected by vacuum filtration
  3. additionAbsolute ethanol (250 mL) was added to the flask
  4. temperaturethe resulting suspension was heated until all of the solids
  5. dissolutiondissolved
  6. temperatureThe clear solution was cooled to rt
  7. customthe desired product slowly crystallized
  8. filtrationthe crystalline solid was collected by vacuum filtration
  9. washrinsed with 100 mL of fresh ethanol
  10. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-2428d42a8b534ac48272bf09610f408e
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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