m-Chloroperbenzoic acid → 1-[2-(4-Allyloxy-phenylmethanesulfinyl)-ethyl]-1H-[1,2,3]triazole

HRID 33493Notes

Reaction equation

HRID 33493 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:15][C:16]1[CH:30]=[CH:29][C:19]([CH2:20][S:21][CH2:22][CH2:23][N:24]2[CH:28]=[CH:27][N:26]=[N:25]2)=[CH:18][CH:17]=1)[CH:13]=[CH2:14]>C(OCC)(=O)C.ClCCl>[CH2:12]([O:15][C:16]1[CH:30]=[CH:29][C:19]([CH2:20][S:21]([CH2:22][CH2:23][N:24]2[CH:28]=[CH:27][N:26]=[N:25]2)=[O:9])=[CH:18][CH:17]=1)[CH:13]=[CH2:14]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 222420761-[2-(4-Allyloxy-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole

Product 1

HCID 222420851-[2-(4-Allyloxy-phenylmethanesulfinyl)-ethyl]-1H-[1,2,3]triazoleYield 62.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.86 g (8.29 mmol) 77% 3-chloroperbenzoic acid in 40 ml ethyl acetate was added at −30° C. within 20 min. to a solution of 1.90 g (6.90 mmol) 1-[2-(4-allyloxy-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole in 160 ml dichloromethane and stirred for 1 h. The mixture was allowed to warm to room temperature (r.t.) washed with sat. NaHCO3-solution, water and evaporated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol 5:1) to give 1.25 g of the title compound as white powder.

Workup

  1. washwashed with sat. NaHCO3-solution, water
  2. customevaporated
  3. customThe residue was purified by chromatography on silica gel (ethyl acetate/methanol 5:1)

Sources & evidence

ORD record
ord-949ee3ff62fd4c5ca41768ef2de67233
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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