Sodium Bicarbonate → HCID 67548184, compound

HRID 2356713Notes

Reaction equation

HRID 2356713 reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[S:8][C:7]([C:9]2[NH:10][C:11]([CH2:20]Cl)=[C:12]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[N:13]=2)=[CH:6][CH:5]=1.[C:22](=O)([O-])[OH:23].[Na+]>CO>[ClH:3].[ClH:1].[Cl:3][C:4]1[S:8][C:7]([C:9]2[NH:10][C:11]([CH2:20][O:23][CH3:22])=[C:12]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[N:13]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67547600HCID 67547600, compound

Product 1

HCID 67548184HCID 67548184, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (10 ml) was dissolved a crude product of 2-(5-chlorothiophen-2-yl)-5-chloromethyl-4-(3-pyridyl)-imidazole dihydrochloride (260 mg) and the mixture was refluxed for 2 hours. After cooling, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with a mixed solution of ethyl acetate-tetrahydrofuran. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=40:1), and then, treated with hydrogen chloride-dioxane solution to obtain 2-(5-chlorothiophen-2-yl)-5-methoxymethyl-4-(3-pyridyl) imidazole dihydrochloride (63 mg) as pale yellowish powder.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with a mixed solution of ethyl acetate-tetrahydrofuran
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=40:1)
  8. additiontreated with hydrogen chloride-dioxane solution

Sources & evidence

ORD record
ord-1e2b128161704151a009fbf5103e48b8
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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