Sodium Thiosulfate → HCID 80632486, compound

HRID 1747536Notes

Reaction equation

HRID 1747536 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[N:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[N:3]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]=[O:14])=[CH:11][N:12]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 61255848HCID 61255848, compound

Product 1

HCID 80632486HCID 80632486, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (5 mL) was dissolved (6-(2-methyl-1H-imidazol-1-yl)pyridin-3-yl)methanol (340 mg, 1.80 mmol) obtained in Step 2. Dess-Martin periodinane (915 mg, 2.16 mmol) was added and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution and the mixture was stirred at room temperature for 1 hour. Extraction with dichloromethane and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=19/1) to give 6-(2-methyl-1H-imidazol-1-yl)nicotinaldehyde (292 mg, 87% yield).

Workup

  1. extractionExtraction with dichloromethane
  2. dry with materialdrying over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. customthe solvent in the filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=19/1)

Sources & evidence

ORD record
ord-85548ffeeedb4dc6ba84f72013ee4977
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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