m-Chloroperbenzoic acid → 2-[(Imidazo[1,2-a]pyridin-3-yl)methanesulfinyl]-1H-benzimidazole

HRID 2414081Notes

Reaction equation

HRID 2414081 reaction equation
[N:1]1[CH:2]=[C:3]([CH2:10][S:11][C:12]2[NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[N:13]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.ClC1C=CC=C(C(OO)=[O:29])C=1>ClCCl>[N:1]1[CH:2]=[C:3]([CH2:10][S:11]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[N:13]=2)=[O:29])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14032981HCID 14032981, compound

Product 1

HCID 140329822-[(Imidazo[1,2-a]pyridin-3-yl)methanesulfinyl]-1H-benzimidazoleYield 21.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 150 mg (0.54 mmole) of 2-[(imidazo[1,2-a]pyridin-3-ylmethyl)thio]-1H-benzimidazole (see Example 1) in 4.0 ml of dichloromethane was cooled in an ice bath. A solution of 120 mg (0.59 mmole) of ca. 85% m-chloroperbenzoic acid in the minimum amount of dichloromethane needed to form a solution was then added dropwise with stirring. The reaction was quenched with a few drops of dimethylsulfide. The mixture was washed with saturated aqueous sodium bicarbonate. The organic phase was concentrated in vacuo and chromatographed on silica gel (using ethanol-dichloromethane-triethylamine as eluent) to yield 35 mg of the title compound. Structure assignment was supported by the nmr and infrared spectra and by elemental analysis.

Workup

  1. temperaturewas cooled in an ice bath
  2. customto form a solution
  3. additionwas then added dropwise
  4. customThe reaction was quenched with a few drops of dimethylsulfide
  5. washThe mixture was washed with saturated aqueous sodium bicarbonate
  6. concentrationThe organic phase was concentrated in vacuo
  7. customchromatographed on silica gel (using ethanol-dichloromethane-triethylamine as eluent)

Sources & evidence

ORD record
ord-122f3f588a65471e959b701270299f33
Source dataset
uspto-grants-1988_01
Patent number
US04721718

Reaction notes

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