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

HRID 892250Notes

Reaction equation

HRID 892250 reaction equation
[CH2:1]([O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][S:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].ClC1C=C(C(OO)=[O:28])C=CC=1>ClCCl.C(OCC)(=O)C>[CH2:1]([O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][S:10]([CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[O:28])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

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

To a solution of 1.90 g (6.9 mmol) 1-[2-(4-all yloxy-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole in 150 ml dichloromethane was added dropwise at −30° C. a solution of 1.86 g (8.3 mmol) 3-chloro-benzenecarboperoxoic acid in 40 ml ethyl acetate and stirring continued for 1 hour. The mixture was allowed to warm up over night, washed with sodium bicarbonate and sodium carbonate solution, then with water, dried and evaporated. Elution form silica with ethyl acetate/methanol 5:1 furnished 1.25 g (62%) 1-[2-(4-allyloxy-phenylmethanesulfinyl)-ethyl]-1H-[1,2,3]triazole as white solid.

Workup

  1. temperatureto warm up over night
  2. washwashed with sodium bicarbonate and sodium carbonate solution
  3. dry with materialwith water, dried
  4. customevaporated
  5. washElution
  6. customform silica with ethyl acetate/methanol 5:1

Sources & evidence

ORD record
ord-24a871f412714e10b75d2d71d232cf4d
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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