m-Chloroperbenzoic acid → 4,5-Bis-(4-methoxyphenyl)-1-benzyl-2-(4-methylphenylsulfinyl)imidazole

HRID 370800Notes

Reaction equation

HRID 370800 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:40][C:41]3[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=3)[N:23]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[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>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:21]=[C:22]([S:40]([C:41]3[CH:42]=[CH:43][C:44]([CH3:47])=[CH:45][CH:46]=3)=[O:9])[N:23]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12832377HCID 12832377, compound

Product 1

HCID 128323784,5-Bis-(4-methoxyphenyl)-1-benzyl-2-(4-methylphenylsulfinyl)imidazoleYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.08 g of 3-chloroperbenzoic acid (80%) in 100 ml of dichloromethane is added dropwise to a solution of 2.46 g of 4,5-bis(4-methoxyphenyl)-1-benzyl-2-(4-methylphenylthio)imidazole in 50 ml of dichloromethane. The mixture is stirred 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 chromatographed on 150 g of silica gel with ethyl acetate/hexane 2:3, thus producing 2.17 g of 4,5-bis-(4-methoxyphenyl)-1-benzyl-2-(4-methylphenylsulfinyl)imidazole as an amorphous foam.

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 chromatographed on 150 g of silica gel with ethyl acetate/hexane 2:3

Sources & evidence

ORD record
ord-23d1b29c2bc84b74af1e56203ee7ced1
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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