Water → HCID 55240554, compound

HRID 1747534Notes

Reaction equation

HRID 1747534 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[H-].[Na+].Cl[C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:11]=1.O>CS(C)=O>[CH3:1][C:2]1[N:3]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:11]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 55240554HCID 55240554, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In DMSO (5 mL) was dissolved 2-methyl-1H-imidazole (575 mg, 7.00 mmol). To the solution 60% sodium hydride (in oil) (323 mg, 8.08 mmol) was added at 0° C. and the mixture was stirred at room temperature for 30 minutes. Ethyl 6-chloronicotinate (1.00 g, 5.39 mmol) was added and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=97/3) to give ethyl 6-(2-methyl-1H-imidazol-1-yl)nicotinate (455 mg, 37% yield).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionExtraction with ethyl acetate
  3. washwashing with saturated brine
  4. dry with materialdrying over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=97/3)

Sources & evidence

ORD record
ord-d83e8d490e5249839e5f8451677a46fa
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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