m-Chloroperbenzoic acid → HCID 12832335, compound

HRID 1995209Notes

Reaction equation

HRID 1995209 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]([Cl:40])=[C:36]([Cl:41])[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:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=3)=[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 20275409HCID 20275409, compound

Product 1

HCID 12832335HCID 12832335, compoundYield 88.6%

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 4.57 g of 4,5-bis(4-methoxyphenyl)-2-(3,4-dichlorophenylthio)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 2:3, thus obtaining 4.19 g of 4,5-bis(4-methoxyphenyl)-2-(3,4-dichlorophenylsulfinyl)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 2:3

Sources & evidence

ORD record
ord-ce806c3de08549a39a7e72e2b6f0e881
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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