m-Chloroperbenzoic acid → HCID 178493207, compound

HRID 505382Notes

Reaction equation

HRID 505382 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[NH:9][C:10]([S:12][CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[CH:17]=[CH:16][N:15]=3)=[N:11][C:6]2=[CH:5][C:4]=1[CH3:23].ClC1C=CC=C(C(OO)=[O:32])C=1.C(=O)(O)[O-].[Na+]>CO.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[NH:9][C:10]([S:12]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[CH:17]=[CH:16][N:15]=3)=[O:32])=[N:11][C:6]2=[CH:5][C:4]=1[CH3:23]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178493198HCID 178493198, compound

Product 1

HCID 178493207HCID 178493207, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
-30 °C

Procedure

5-Methoxy-2-(((4-methoxy-3-methyl-2-pyridinyl)methyl)thio)-6-methyl-3H-imidazo[4,5-b]pyridine (784 mg, 2.37 mmol) was dissolved in a mixture of methanol (6 ml) and toluene (54 ml). Metachloroperbenzoic acid (566 mg) in a mixture solution of methanol (3 ml) and toluene (3 ml) were added thereto at −40° C. under nitrogen flow, and the reaction mixture was stirred at −20 to −40° C. for 2 hours. After the reaction was completed, a sodium bicarbonate solution was added, and the organic layer was separated. The aqueous layer was extracted with chloroform (40 ml), combined with the organic layer and dried over sodium sulfate, the solvent was evaporated and the residue was obtained which was then precipitated as a solid from a mixture of chloroform and ether, thereby yielding the title compound (654 mg, 1.89 mmol, 80%) as a purple gray solid.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with chloroform (40 ml)
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated
  5. customthe residue was obtained which
  6. customwas then precipitated as a solid from a mixture of chloroform and ether

Sources & evidence

ORD record
ord-2568e47dce054823b8d47ac02a600c81
Source dataset
uspto-grants-2010_08
Patent number
US07781452B2

Reaction notes

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