Calcium Chloride → HCID 22938658, compound

HRID 856797Notes

Reaction equation

HRID 856797 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-])=O)=[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:9]1[CH:8]=[CH:7][C:6]2[N:2]([CH3:1])[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:4][C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 22938679HCID 22938679, compound

Product 1

HCID 22938658HCID 22938658, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of 1-methyl-5-nitro-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole (700 mg), reduced iron (0.6 g) and anhydrous calcium chloride (1.18 g) in 85% ethanol (15 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. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:8) to give 5-amino-1-methyl-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole (123 mg) as brown 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 silica gel column chromatography (methanol:ethyl acetate=1:8)

Sources & evidence

ORD record
ord-dd6a3f9ed9f64b3ba24ee51e40b325a7
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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