Sodium Hydroxide → 5-Nitro-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole

HRID 856741Notes

Reaction equation

HRID 856741 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+].Cl.Cl[CH2:18][C:19]1[N:23]([CH2:24][CH2:25][CH3:26])[CH:22]=[N:21][CH:20]=1>C(O)C>[N+:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([S:1][CH2:18][C:19]3[N:23]([CH2:24][CH2:25][CH3:26])[CH:22]=[N:21][CH:20]=3)[NH:3][C:4]=2[CH:10]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 229386165-(chloromethyl)-1-propyl-1H-imidazole hydrochlorideHCID 178526473HCID 178526473, compound

Product 1

HCID 229387045-Nitro-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazoleYield 49.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-mercapto-5-nitrobenzimidazole (2.0 g) was dissolved in ethanol (20 ml), 3N sodium hydroxide (8.2 ml) was added to the mixture, 5-chloromethyl-1-propylimidazole hydrochloride (2.2 g) was added to the mixture, and the mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, and to the obtained residue was added water, and the mixture was 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]thio]benzimidazole (1.6 g).

Workup

  1. additionwas added to the mixture
  2. customThe solvent was removed under reduced pressure
  3. additionto the obtained residue was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-18636e1d77a449fe838c293fca58ea79
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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