m-Chloroperbenzoic acid → 2-(4-Fluorobenzene-1-sulfinyl)-4,5-bis(4-methoxyphenyl)-1H-imidazole

HRID 1995210Notes

Reaction equation

HRID 1995210 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][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>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:21]=[C:22]([S:33]([C:34]3[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=3)=[O:9])[NH:23][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 128323082-[(4-Fluorophenyl)sulfanyl]-4,5-bis(4-methoxyphenyl)-1H-imidazole

Product 1

HCID 128323372-(4-Fluorobenzene-1-sulfinyl)-4,5-bis(4-methoxyphenyl)-1H-imidazoleYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.164 g of 3-chloroperbenzoic acid (80%) in 150 ml of dichloromethane is dropped to a solution of 4.07 g of 4,5-bis(4-methoxyphenyl)-2-(4-fluorophenylthio)imidazole in 100 ml of dichloromethane. The solution is stirred for 3 hours at room temperature, 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 acetone/hexane, thus obtaining 3.86 g of 4,5-bis(4-methoxyphenyl)-2-(4-fluorophenylsulfinyl)imidazole as an amorphous foam.

Workup

  1. washwashed 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 acetone/hexane

Sources & evidence

ORD record
ord-0a080d5033de4627bc0c6d47cf3b83aa
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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