Potassium Iodide → 1-[4-(4-{2-[(e)-2-(-4-Trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1h-[1,2,3]triazole

HRID 750949Notes

Reaction equation

HRID 750949 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:24][C:25]1[N:26]=[C:27]([CH:30]=[CH:31][C:32]2[CH:37]=[CH:36][C:35]([S:38]([C:40]([F:43])([F:42])[F:41])=[O:39])=[CH:34][CH:33]=2)[O:28][CH:29]=1.[I-].[K+]>CC(=O)CC.ClCCl.CO>[F:43][C:40]([F:41])([F:42])[S:38]([C:35]1[CH:36]=[CH:37][C:32](/[CH:31]=[CH:30]/[C:27]2[O:28][CH:29]=[C:25]([CH2:24][O:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[N:2]4)=[CH:15][CH:14]=3)[N:26]=2)=[CH:33][CH:34]=1)=[O:39]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole

Product 1

HCID 114892071-[4-(4-{2-[(e)-2-(-4-Trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1h-[1,2,3]triazoleYield 72.3%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.815 g (3.75 mmol) 4-(4-[1,2,3]triazol-1-yl-butyl)-phenol and 0.815 g (2.50 mmol) cesium carbonate in 15 ml butanone was stirred at 60° C. for 30 min, then 1.40 g (4.17 mmol) 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole and 0.692 g (4.17 mmol) potassium iodide were added and stirring at 60° C. continued for 40 hours. After evaporation, 50 ml water was added and the mixture extracted with two portions of 50 ml ethyl acetate. The combined organic layers were washed with 1N sodium hydroxide and water, dried over sodium sulfate and evaporated to give 2.20 g raw product. After chromatography on silica, eluent dichloromethane/methanol 20:1, resulted 1.40 g (72%) pure title compound as tan crystals melting at 122-123° C.

Workup

  1. stirringstirring at 60° C.
  2. waitcontinued for 40 hours
  3. customAfter evaporation, 50 ml water
  4. additionwas added
  5. extractionthe mixture extracted with two portions of 50 ml ethyl acetate
  6. washThe combined organic layers were washed with 1N sodium hydroxide and water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto give 2.20 g raw product

Sources & evidence

ORD record
ord-86f3676c853e4b1aaf7b8d4fd52db292
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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