Calcium Chloride → 6-Amino-1-methyl-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole

HRID 856798Notes

Reaction equation

HRID 856798 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[S:14][CH2:15][C:16]1[N:20]([CH2:21][CH2:22][CH3:23])[CH:19]=[N:18][CH:17]=1.[Cl-].[Ca+2].[Cl-]>C(O)C>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]2[N:4]=[C:3]([S:14][CH2:15][C:16]3[N:20]([CH2:21][CH2:22][CH3:23])[CH:19]=[N:18][CH:17]=3)[N:2]([CH3:1])[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 229384591-Methyl-6-nitro-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole

Product 1

HCID 229388936-Amino-1-methyl-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazoleYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of 1-methyl-6-nitro-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole (230 mg), reduced iron (194 mg) and anhydrous calcium chloride (38.5 mg) in 85% ethanol (10 ml) was stirred for 1 day under nitrogen atmosphere at 105° C. The mixture was allowed to be at room temperature, the insolubles were filtered off, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate) to give 6-amino-1-methyl-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole (170 mg) as colorless oil.

Workup

  1. customto be at room temperature
  2. filtrationthe insolubles were filtered off
  3. additionwater was added to the mixture
  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. distillationthe solvent was distilled off under reduced pressure
  8. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b871b540f86049308b0d46d06656393e
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…