Water → 5-Nitro-2-[[(1-propylimidazol-5-yl)methyl]sulfanyl]pyridine

HRID 856732Notes

Reaction equation

HRID 856732 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:19][C:20]1[N:24]([CH2:25][CH2:26][CH3:27])[CH:23]=[N:22][CH:21]=1.O>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:19][C:20]2[N:24]([CH2:25][CH2:26][CH3:27])[CH:23]=[N:22][CH:21]=2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 229386165-(chloromethyl)-1-propyl-1H-imidazole hydrochlorideHCID 178526723C5H4N2O2S

Product 1

HCID 695224915-Nitro-2-[[(1-propylimidazol-5-yl)methyl]sulfanyl]pyridineYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-mercapto-5-nitropyridine (2.3 g) was dissolved in DMF (47 ml), potassium carbonate (6.2 g) and 5-chloromethyl-1-propylimidazole hydrochloride (3.5 g) was added to the mixture, and the mixture was stirred for 40 hours at room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 5-nitro-2-[[(1-propylimidazol-5-yl)methyl]sulfanyl]pyridine (2.9 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4cbe4969e7794837beba0b1ff692107b
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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