m-Chloroperbenzoic acid → HCID 22388366, compound

HRID 1072901Notes

Reaction equation

HRID 1072901 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([S:23][CH3:24])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18].ClC1C=CC=C(C(OO)=[O:33])C=1>ClCCl.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:22]=[C:21]([S:23]([CH3:24])=[O:33])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22387771HCID 22387771, compound

Product 1

HCID 22388366HCID 22388366, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(2-chloro-4-(methylthio)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (148 mg) in dichloromethane (2.8 ml) was added m-chloroperbenzoic acid (81 mg) under ice-cooling, and the mixture was stirred for 1 hr. The reaction mixture was diluted with chloroform, washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and acetonitrile was added to the residue for crystallization, whereby the objective compound (118 mg) was obtained as a white powder.

Workup

  1. temperaturecooling
  2. washwashed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. additionacetonitrile was added to the residue for crystallization, whereby the objective compound (118 mg)
  6. customwas obtained as a white powder

Sources & evidence

ORD record
ord-4bb4a9f9775a4b03a18ff1defabe8cf4
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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