m-Chloroperbenzoic acid → 1,5-bis(4-methoxyphenyl)-3-(methylsulfinyl)-1H-1,2,4-triazole

HRID 584734Notes

Reaction equation

HRID 584734 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[N:12][C:11]([S:22][CH3:23])=[N:10]2)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[N:12][C:11]([S:22]([CH3:23])=[O:32])=[N:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 99234391,5-bis(4-methoxyphenyl)-3-(methylthio)-1H-1,2,4-triazole

Product 1

HCID 102689921,5-bis(4-methoxyphenyl)-3-(methylsulfinyl)-1H-1,2,4-triazoleYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,5-bis(4-methoxyphenyl)-3-(methylthio)-1H-1,2,4-triazole (150 mg, 0.458 mmol) and m-chloroperbenzoic acid (119 mg, 0.687 mmol) in dichloromethane (1.5 mL) was stirred for 3 hours at room temperature. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane-2% methanol in dichloromethane) to give 1,5-bis(4-methoxyphenyl)-3-(methylsulfinyl)-1H-1,2,4-triazole (152 mg, 96.6% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (dichloromethane-2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-92e94423cff24bff9c8c34690fe800d2
Source dataset
uspto-grants-2005_08
Patent number
US06927230B2

Reaction notes

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