m-Chloroperbenzoic acid → HCID 12832363, compound

HRID 1995223Notes

Reaction equation

HRID 1995223 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:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:23]([CH3:33])[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:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:9])[N:23]([CH3:33])[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 20275411HCID 20275411, compound

Product 1

HCID 12832363HCID 12832363, compoundYield 72.8%

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 4.03 g of 4,5-bis(4-methoxyphenyl)-2-phenylthio-1-methylimidazole in 100 ml of dichloromethane. The solution is agitated 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 200 g of silica gel with ethyl acetate/cyclohexane 2:3, thus obtaining 3.05 g of 4,5-bis(4-methoxyphenyl)-2-phenylsulfinyl-1-methylimidazole, which has a melting point of 114°-115° after recrystallization from dichloromethane/ether.

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 200 g of silica gel with ethyl acetate/cyclohexane 2:3

Sources & evidence

ORD record
ord-278f20125e2a49208f0e740097da06e7
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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