Sodium Thiosulfate Pentahydrate → HCID 68486879, compound

HRID 2194715Notes

Reaction equation

HRID 2194715 reaction equation
[ClH:1].Cl.[CH3:3][NH:4][CH2:5][C:6]1[N:7]=[C:8]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1.[OH:24]OS([O-])=O.[K+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>CC(C)=O.O>[ClH:1].[ClH:1].[CH3:3][NH:4][CH2:5][C:6]1[N:7]=[C:8]([S:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:24])[N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1

Participants

7

Reactant 4

HCID 61475Sodium Thiosulfate PentahydrateHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 67004251HCID 67004251, compound

Product 1

HCID 68486879HCID 68486879, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of N-methyl-1-[1-phenyl-2-(phenylthio)-1H-imidazol-4-yl]methanamine dihydrochloride (70 mg) in acetone (20 mL) and water (10 mL) was added dropwise a solution of oxone (176 mg) in water (10 mL), and the mixture was stirred at room temperature for 5 hr. Sodium thiosulfate pentahydrate (1 g) was added to the reaction mixture and the mixture was stirred for 1 hr. A saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with a mixed solution of ethyl acetate-tetrahydrofuran (1:1). The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=1:0→7:3) and dissolved in methanol (5 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added, and the mixture was concentrated under reduced pressure. The residue was dissolved in a mixed solution of methanol-tetrahydrofuran, and ethyl acetate was added. The precipitated insoluble materials were collected by filtration to give the title compound as a colorless powder (yield 34 mg, yield 47%).

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. extractionthe mixture was extracted with a mixed solution of ethyl acetate-tetrahydrofuran (1:1)
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=1:0→7:3)
  6. dissolutiondissolved in methanol (5 mL)
  7. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added
  8. concentrationthe mixture was concentrated under reduced pressure
  9. dissolutionThe residue was dissolved in a mixed solution of methanol-tetrahydrofuran, and ethyl acetate
  10. additionwas added
  11. filtrationThe precipitated insoluble materials were collected by filtration

Sources & evidence

ORD record
ord-a72a0388e8d44d00b5ccd6ce50201ee5
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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