Sodium Thiosulfate → HCID 117842938, compound

HRID 2208997Notes

Reaction equation

HRID 2208997 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](SC)[C:5]2[N:10]([CH2:13][CH3:14])[CH:11]=[N:12][C:4]=2[CH:3]=1.[Cl:15][C:16]1[N:21]=[C:20](SC)[C:19]2[N:24]=[CH:25][N:26]([CH2:27][CH3:28])[C:18]=2[CH:17]=1.[CH:29]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:40][S:41]([O-:44])(=S)=O.[Na+].[Na+]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([S:41]([CH3:16])(=[O:44])=[O:40])[C:5]2[N:10]([CH2:13][CH3:14])[CH:11]=[N:12][C:4]=2[CH:3]=1.[Cl:15][C:16]1[N:21]=[C:20]([S:41]([CH3:29])(=[O:44])=[O:40])[C:19]2[N:24]=[CH:25][N:26]([CH2:27][CH3:28])[C:18]=2[CH:17]=1

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 117843195HCID 117843195, compoundHCID 117844200HCID 117844200, compound

Product 2

HCID 117842938HCID 117842938, compoundHCID 117843856HCID 117843856, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloro-3-ethyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.13 and 6-chloro-1-ethyl-4-(methylthio)-1H-imidazo[4,5-c]pyridine 2.14 (306 mg, 1.34 mmol) in dichloromethane (10 mL) at 0° C., was added mCPBA (≦77%, 557 mg) and mixture was warmed to room temperature. After 2 h, a 20% solution of Na2S2O3 (aq) (20 mL) was added and reaction mixture was stirred at room temperature for 15 minutes. Then the mixture was taken up in ethyl acetate (150 mL) and washed with saturated NaHCO3 (aq) and brine. The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluted with 0-20% methanol in ethyl acetate) to yield 6-chloro-3-ethyl-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine 2.15 and 6-chloro-1-ethyl-4-(methylsulfonyl)-1H-imidazo[4,5-c]pyridine 2.16.

Workup

  1. customreaction mixture
  2. washwashed with saturated NaHCO3 (aq) and brine
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluted with 0-20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-f0d390f83d4545c8be49939341f43586
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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