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

HRID 1995216Notes

Reaction equation

HRID 1995216 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][C:37]([F:40])=[CH:36][C:35]=3[F:41])[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>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:21]=[C:22]([S:33]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=3[F:41])=[O:9])[NH:23][C:24]=2[C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 128323094,5-Bis(4-methoxyphenyl)-2-(2,4-difluorophenylthio)imidazole

Product 1

HCID 128323494,5-Bis(4-methoxyphenyl)-2-(2,4-difluorophenylsulfinyl)imidazoleYield 73.9%

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 4.25 g of 4,5-bis(4-methoxyphenyl)-2-(2,4-difluorophenylthio)imidazole in 100 ml of dichloromethane. The mixture is agitated for 3 hours at room temperature, the solution washed with sodium bicarbonate solution, dried over sodium sulfate, and concentrated under vacuum to dryness. The residue is chromatographed on 150 g of silica gel with acetone/hexane, thus producing 3.26 g of 4,5-bis(4-methoxyphenyl)-2-(2,4-difluorophenylsulfinyl)imidazole as an amorphous foam.

Workup

  1. washthe solution washed with sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum to dryness
  4. customThe residue is chromatographed on 150 g of silica gel with acetone/hexane

Sources & evidence

ORD record
ord-683dc1c61a284309a14ef80559484f4d
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

Loading…