Acetic Acid → HCID 69023094, compound

HRID 2192231Notes

Reaction equation

HRID 2192231 reaction equation
[CH2:1]([N:8]1[C:20]2[C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1SC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](O)(=O)C.[Mn]([O-])(=O)(=O)=O.[K+].[S:33](=[O:36])(O)[O-:34].[Na+]>O>[CH2:1]([N:8]1[C:20]2[C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1[S:33]([CH3:23])(=[O:36])=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 69023732HCID 69023732, compound

Product 1

HCID 69023094HCID 69023094, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1-benzyl-2-methylsulfanyl-1H-imidazo[4,5-c][1,5]naphthyridine (1 g, 3.2 mmol) was added acetic acid (15 mL), and the white suspension was stirred for a few minutes. To this suspension was added potassium permanganate solution (0.87 g, 5.5 mmol, in water (15 mL)) in a dropwise manner, and the reaction was stirred at room temperature for 2 hours. To the reaction mixture was added sodium bisulfite (0.83 g) and the white suspension was stirred for several minutes. Water was added to this suspension and the reaction mixture was transferred to a separatory funnel. The product was extracted from the aqueous layer with several batches of dichloromethane. The dichloromethane layers were combined, dried (MgSO4), filtered, and evaporated, and the resultant solid washed with ether to afford 1-benzyl-2-methanesulfonyl-1H-imidazo[4,5-c][1,5]naphthyridine as a white solid (0.9 g), mp 187-191° C.; MS (ESI) m/z 339 (M+H); Anal. Calcd for C17H14N4O2S: C, 60.34; H, 4.17; N, 16.56. Found C, 60.45; H, 3.97; N, 16.52.

Workup

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. stirringthe white suspension was stirred for several minutes
  3. customthe reaction mixture was transferred to a separatory funnel
  4. extractionThe product was extracted from the aqueous layer with several batches of dichloromethane
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. washthe resultant solid washed with ether

Sources & evidence

ORD record
ord-af3b87ff2bf44ee2bffb8b6a646b6072
Source dataset
uspto-grants-2012_12
Patent number
US08329721B2

Reaction notes

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