Dimethylformamide → HCID 57974723, compound

HRID 1864723Notes

Reaction equation

HRID 1864723 reaction equation
CN(C=O)C.[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Cl)([O-:25])=[O:24]>O>[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 12078alpha-Chloro-m-nitrotolueneHCID 3168174-(1H-Imidazol-2-yl)-pyridine

Product 1

HCID 57974723HCID 57974723, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

DMF (20 mL) is added to 4-(1H-Imidazol-2-yl)-pyridine (930 mg, 6.4 mmol), sodium carbonate (1.92 g, 20 mmol), and 3-nitrobenzyl chloride (1.71 g, 10 mmol) and the mixture is warmed to 50° C. for 4 h. Water (100 mL) is added and the corresponding mixture is extracted with EtOAc (100 mL), dried over anhydrous sodium sulfate, and crude solution is concentrated under reduced pressure. The organics are dissolved in DCM and filtered through a plug of silica eluting first with DCM, and then washing with 20% MeOH:80% DCM to afford 4-[1-(3-Nitro-benzyl)-1H-imidazol-2-yl]-pyridine as an off-white solid.

Workup

  1. extractionthe corresponding mixture is extracted with EtOAc (100 mL)
  2. dry with materialdried over anhydrous sodium sulfate, and crude solution
  3. concentrationis concentrated under reduced pressure
  4. dissolutionThe organics are dissolved in DCM
  5. filtrationfiltered through a plug of silica eluting first with DCM
  6. washwashing with 20% MeOH

Sources & evidence

ORD record
ord-8225807d2eca4f4dadf558460b50365f
Source dataset
uspto-grants-2009_12
Patent number
US07625931B2

Reaction notes

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