Imidazole → Pyridine, 2-(1H-imidazol-1-yl)-, 1-oxide

HRID 1838245

Reaction equation

HRID 1838245 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Li+].Cl.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N+:11]=1[O-:16]>CN(C)C=O>[N:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N+:11]=2[O-:16])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 62714Lithium hydrideHCID 27240442-Bromopyridine 1-oxide hydrochloride

Product 1

HCID 69108575Pyridine, 2-(1H-imidazol-1-yl)-, 1-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A 0.76 g portion of imidazole was added to 7 ml of N,N-dimethylformamide and mixed with 0.2 g of 90% lithium hydride under ice-cooling and then the mixture was stirred for 40 minutes. Next, 2.17 g of 2-bromopyridine N-oxide hydrochloride was gradually added thereto, the mixture was stirred at room temperature for about 1 hour and further heated at 80° C. for about 1 hour, and then the solvent was evaporated and the thus obtained mixture was subjected to a silica gel column chromatography and eluted with chloroform-methanol-28% aqueous ammonia (10:0.9:0.1, v/v/v) to obtain 1.21 g of the title compound as light yellow crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for about 1 hour
  3. customthe solvent was evaporated
  4. washeluted with chloroform-methanol-28% aqueous ammonia (10:0.9:0.1, v/v/v)

Sources & evidence

ORD record
ord-4364c2c3a9a24ba9aa51ccf6def7c34c
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Linked notes

Loading…