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

HRID 854683Notes

Reaction equation

HRID 854683 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)[O: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[O: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 1363552314-(4-[1,2,3]Triazol-1-ylmethyl-oxazol-2-yl)-phenol

Product 1

HCID 112029941-[2-(4-{2-[(e)-2-(4-Trifluoromethyl-phenyl)-vinyl]-thiazol-4-ylmethoxy}-phenyl)-oxazol-4-ylmethyl]-1h-[1,2,3]triazoleYield 67.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.1212 g (0.50 mmol) 4-(4-[1,2,3]triazol-1-ylmethyl-oxazol-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 0.152 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 201 mg raw material which was recrystallised from ethanol to yield 171 mg (67%) 1-[2-(4-{2-[(E)-2-(4-trifluoromethyl-phenyl)-vinyl]-thiazol-4-ylmethoxy}-phenyl)-oxazol-4-ylmethyl]-1H-[1,2,3]triazole as white crystals melting at 179-181° 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 201 mg raw material which
  10. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-b1d742f4d56648759057574e28f1270b
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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