Potassium Hydroxide → 1-(2-methoxy-4-nitrophenyl)-4-methyl-1H-imidazole

HRID 2075982Notes

Reaction equation

HRID 2075982 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1.[OH-].[K+]>CS(C)=O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:17]1[CH:18]=[C:14]([CH3:13])[N:15]=[CH:16]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisoleHCID 178418800HCID 178418800, compound

Product 1

HCID 454801801-(2-methoxy-4-nitrophenyl)-4-methyl-1H-imidazoleYield 45.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-chloro-5-nitroanisol (187 mg, 1 mmol), of 4-methylimidazol (335 mg, 4 mmol) and of potassium hydroxide (99 mg, 1.5 mmol) in DMSO (0.86 mL) was stirred for 5 hours at 80° under an atmosphere of nitrogen. After cooling to room temperature the reaction was poured onto ice/water. A precipitation was formed and the suspension was stirred for 15 minutes. The solid was filtered off, washed with water, dissolved in dichloromethane, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield a yellow solid. The crude product was purified on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (106 mg, 45%) as a pale-yellow solid. Alternatively the product can be also crystallized from the crude material from diethyl ether. MS ISP (m/e): 234.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.97 (d, 1H), 7.96 (s, 1H), 7.83 (s, 1H), 7.42 (d, 1H), 7.00 (s, 1H), 4.00 (s, 3H), 2.31 (s, 3H).

Workup

  1. additionwas poured onto ice/water
  2. customA precipitation
  3. customwas formed
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. dissolutiondissolved in dichloromethane
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure
  10. customto yield a yellow solid
  11. customThe crude product was purified on silica gel

Sources & evidence

ORD record
ord-80859ce2870d46399e5d504efdd401d4
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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