m-Chloroperbenzoic acid → 4,5-Bis(4-methoxyphenyl)-2-(4-pyridylsulfinyl)imidazole

HRID 1995229Notes

Reaction equation

HRID 1995229 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([S:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[NH:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:16][CH:15]=1>ClCCl>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]2[N:23]=[C:22]([S:33]([C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)=[O:9])[NH:21][C:20]=2[C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 128323724,5-Bis(4-methoxyphenyl)-2-(4-pyridylthio)imidazole

Product 1

HCID 128323734,5-Bis(4-methoxyphenyl)-2-(4-pyridylsulfinyl)imidazoleYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.164 g of 3-chloroperbenzoic acid (80%) in 150 ml of dichloromethane is added dropwise to a solution of 3.90 g of 4,5-bis(4-methoxyphenyl)-2-(4-pyridylthio)imidazole in 100 ml of dichloromethane. The mixture is agitated for 3 hours at room temperature, the solution is washed with sodium bicarbonate solution, dried over sodium sulfate, and concentrated to dryness under vacuum. The residue is recrystallized from ethanol/ether, thus producing 3.41 g of 4,5-bis(4-methoxyphenyl)-2-(4-pyridylsulfinyl)imidazole, mp 170°-171°.

Workup

  1. washthe solution is washed with sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness under vacuum
  4. customThe residue is recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-05d038337b5443948d35154137c5321e
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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