m-Chloroperbenzoic acid → 2-[(3,5-Dimethyl-4-methoxy-2-pyridyl)methylsulfinyl]imidazo[4,5-b]pyridine

HRID 1638593Notes

Reaction equation

HRID 1638593 reaction equation
[CH3:1][C:2]1[C:3]([CH2:11][S:12][C:13]2[NH:14][C:15]3[C:16]([N:21]=2)=[N:17][CH:18]=[CH:19][CH:20]=3)=[N:4][CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:11][S:12]([C:13]2[NH:14][C:15]3[C:16]([N:21]=2)=[N:17][CH:18]=[CH:19][CH:20]=3)=[O:30])=[N:4][CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 137682532-[(3,5-Dimethyl-4-methoxy-2-pyridyl)methylthio]-imidazo[4,5-b]pyridine

Product 1

HCID 137682642-[(3,5-Dimethyl-4-methoxy-2-pyridyl)methylsulfinyl]imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.4 Gram of 2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methylthio]imidazo[4,5-b]pyridine was dissolved in 40 ml of chloroform, then this solution was stirred under ice-cooling condition, 0.27 g of m-chloroperbenzoic acid (85%) was added thereto. The whole reaction mixture was stirred at the same temperature for 20 minutes. After the reaction was completed, the reaction mixture was concentrated under reduced pressure, the residue thus obtained was washed with diethyl ether. Recrystallization from ethanol to yield 1.15 g of 2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methylsulfinyl]imidazo[4,5-b]pyridine in the form of light brown powdery crystals. Melting point: 169°-170° C.

Workup

  1. additionwas added
  2. customThe whole reaction mixture
  3. stirringwas stirred at the same temperature for 20 minutes
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customthe residue thus obtained
  6. washwas washed with diethyl ether
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-76e3a0df0b844e9c8b527bfc0d2eec94
Source dataset
uspto-grants-1989_11
Patent number
US04880815

Reaction notes

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