m-Chloroperbenzoic acid → HCID 59656020, compound

HRID 2054560Notes

Reaction equation

HRID 2054560 reaction equation
[C:1]12([C:11]3[N:15]([CH3:16])[C:14]([C:17]4[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=4)=[N:13][N:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)Cl>[C:1]12([C:11]3[N:15]([CH3:16])[C:14]([C:17]4[CH:22]=[CH:21][C:20]([S:23]([CH3:24])=[O:33])=[CH:19][CH:18]=4)=[N:13][N:12]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59656187HCID 59656187, compound

Product 1

HCID 59656020HCID 59656020, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-(1-adamantyl)-4-methyl-5-[4-(methylthio)phenyl]-4H-1,2,4-triazole (4-23) (50 mg, 0.15 mmol) and m-chloroperbenzoic acid (85%, MCPBA) (45 mg, 0.22 mmol) in methylene chloride (0.75 mL) was stirred at room temperature for 25 min. The mixture was diluted with methylene chloride, washed with 10% aqueous K2CO3, water, and saturated brine and dried (MgSO4). The residue after evaporation in vacuo was purified by reverse-phase chromatography on a C-18 silica gel column with an acetonitrile-0.1% trifluoroacetic acid gradient to give 3-(1-adamantyl)-4-methyl-5-[4-(methylsulfinyl)phenyl]-4H-1,2,4-triazole (4-24).

Workup

  1. washwashed with 10% aqueous K2CO3, water, and saturated brine
  2. dry with materialdried (MgSO4)
  3. customThe residue after evaporation in vacuo
  4. customwas purified by reverse-phase chromatography on a C-18 silica gel column with an acetonitrile-0.1% trifluoroacetic acid gradient

Sources & evidence

ORD record
ord-2c6321829cde464db95666083a9efc2e
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Reaction notes

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