Potassium Iodide → 1-[2-(4-{2-[(e)-2-(4-Trifluoromethyl-phenyl)-vinyl]-thiazol-4-ylmethoxy}-phenyl)-thiazole-4-ylmethyl]-1h-[1,2,3]triazole

HRID 854684Notes

Reaction equation

HRID 854684 reaction equation
[N:1]1([CH2:6][C:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[S:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:26][C:27]1[N:28]=[C:29]([CH:32]=[CH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)[S:30][CH:31]=1.[I-].[K+]>CC(=O)CC>[F:43][C:40]([F:41])([F:42])[C:37]1[CH:38]=[CH:39][C:34](/[CH:33]=[CH:32]/[C:29]2[S:30][CH:31]=[C:27]([CH2:26][O:18][C:15]3[CH:16]=[CH:17][C:12]([C:9]4[S:10][CH:11]=[C:7]([CH2:6][N:1]5[CH:5]=[CH:4][N:3]=[N:2]5)[N:8]=4)=[CH:13][CH:14]=3)[N:28]=2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 694286794-Chloromethyl-2-[2-(4-trifluoromethyl-phenyl)-vinyl]-thiazoleHCID 1363552324-(4-[1,2,3]Triazol-1-ylmethyl-thiazol-2-yl)-phenol

Product 1

HCID 114893661-[2-(4-{2-[(e)-2-(4-Trifluoromethyl-phenyl)-vinyl]-thiazol-4-ylmethoxy}-phenyl)-thiazole-4-ylmethyl]-1h-[1,2,3]triazoleYield 33%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.129 g (0.50 mmol) 4-(4-[1,2,3]triazol-1-ylmethyl-thiazol-2-yl)-phenol and 0.10 g (0.30 mmol) cesium carbonate in 10 ml butanone was stirred at 60° C. for 30 min, then 0.153 g (0.50 mmol) 4-chloromethyl-2-[2-(4-trifluoromethyl-phenyl)-vinyl]-thiazole and 0.083 g (0.50 mmol) potassium iodide were added and stirring at 60° C. continued over night. After evaporation, 15 ml water was added and the mixture extracted with two portions of 15 ml ethyl acetate. The combined organic layers were washed with 1N sodium hydroxide and water, dried over sodium sulfate and evaporated to give 174 mg raw material which was purified on silica. Elution with ethyl acetate/heptane 5:1 yielded 86 mg white crystals (33%) of 1-[2-(4-{2-[2-((E)-4-trifluoromethyl-phenyl)-vinyl]-thiazol-4-ylmethoxy}-phenyl)-thiazol-4-ylmethyl]-1H-[1,2,3]triazole melting at 146-148° C.

Workup

  1. stirringstirring at 60° C.
  2. waitcontinued over night
  3. customAfter evaporation, 15 ml water
  4. additionwas added
  5. extractionthe mixture extracted with two portions of 15 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 174 mg raw material which
  10. customwas purified on silica
  11. washElution with ethyl acetate/heptane 5:1

Sources & evidence

ORD record
ord-a97f041e92084fbfb3135f8168df8f65
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

Loading…