Imidazole → HCID 18953543, compound

HRID 257416Notes

Reaction equation

HRID 257416 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.C(N(CC)CC)C>O1CCOCC1>[N:11]1([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8471TriethylamineHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 18953543HCID 18953543, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-3-nitropyridine (2.00 g, 12.6 mmol) and imidazole (2.25 g, 33.0 mmol) were dissolved in 10 ml of 1,4-dioxane, and 2 ml of triethylamine was added thereto, followed by reaction at 90° to 100° C. for 1.5 hours. Then, the solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: dichloromethane:methanol=10:1 (v/v)] to obtain 2.31 g of a yellow liquid (yield: 96.4%).

Workup

  1. customfollowed by reaction at 90° to 100° C. for 1.5 hours
  2. customThen, the solvent was removed by distillation under reduced pressure
  3. customthe residue was purified by silica gel column chromatography [eluent: dichloromethane:methanol=10:1 (v/v)]

Sources & evidence

ORD record
ord-6adec537ab4744ba99ae6ece8f185091
Source dataset
uspto-grants-1993_11
Patent number
US05262415

Reaction notes

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