m-Chloroperbenzoic acid → HCID 12832370, compound

HRID 1995227Notes

Reaction equation

HRID 1995227 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([S:31][C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[NH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[CH:15][CH:14]=1>ClCCl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([S:31]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[O:9])[NH:22][C:23]=2[C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12832369HCID 12832369, compound

Product 1

HCID 12832370HCID 12832370, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.164 g of 3-chloroperbenzoic acid (80%) in 150 ml of dichloromethane is added dropwise to a solution of 4.90 g of 4,5-bis(4-chlorophenyl)-2-(2-thienylthio)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, yielding 3.83 g of 4,5-bis(4-chlorophenyl)-2-(2-thienylsulfinyl)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-c319dc64aa0f41828f744a5abaa3d428
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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