Trimethylsulfonium iodide → 1-(4-Chloro-2-oxiranyl-phenoxymethyl)-1H-benzotriazole

HRID 1929081Notes

Reaction equation

HRID 1929081 reaction equation
[N:1]1([CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:13]=2[CH:14]=[O:15])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[I-].[CH3:22][S+](C)C>C(Cl)Cl.[OH-].[Na+].[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:20][C:17]1[CH:18]=[CH:19][C:12]([O:11][CH2:10][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[N:2]2)=[C:13]([CH:14]2[CH2:22][O:15]2)[CH:16]=1

Participants

6

Reactant 2

HCID 75127Trimethylsulfonium iodideHCID 50961702-(Benzotriazol-1-ylmethoxy)-5-chloro-benzaldehyde

Product 1

HCID 37578321-(4-Chloro-2-oxiranyl-phenoxymethyl)-1H-benzotriazoleYield 114.8%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

98 (15.5 g, 54 mmol) is dissolved in 150 ml of DCM and 150 ml of 40% aqueous sodium hydroxide solution. After addition of trimethylsulfonium iodide (14.3 g, 70.2 mmol) and tetrabutylammoniumiodide (1.4 g, 3.8 mmol), the mixture is refluxed for 18 h. The reaction mixture is diluted with DCM, washed with water and the organic layers are dried over Na2SO4. Evaporation gave 18.7 g of a yellow oil, which is further purified by flash-chromatography (silicagel, ethyl acetate/hexanes 3:7)

Workup

  1. temperaturethe mixture is refluxed for 18 h
  2. washwashed with water
  3. dry with materialthe organic layers are dried over Na2SO4
  4. customEvaporation

Sources & evidence

ORD record
ord-deb1196ca8364d3e99cbe7c2fb8759ed
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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