Potassium Iodide → HCID 11249576, compound

HRID 750978Notes

Reaction equation

HRID 750978 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)[S:28][CH:29]=1.[I-].[K+]>CC(=O)CC>[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[S: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

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 69290058HCID 69290058, compound

Product 1

HCID 11249576HCID 11249576, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.11 g (0.49 mmol) 4-(4-[1,2,3]triazol-1-yl-butyl)-phenol and 0.10 g (0.30 mmol) cesium carbonate in 10 ml butanone was stirred at 60° C. for 30 min, then 0.15 g (0.49 mmol) 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-thiazole and 0.08 g (0.49 mmol) potassium iodide were added and stirring at 60° C. continued for 3 days. 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, after purification on silica (ethyl acetate/heptane 1:1, then ethyl acetate) 90 mg (34%) 1-[4-(4-{2-[(E)-2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-thiazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole as white crystals melting at 118-119° C.

Workup

  1. stirringstirring at 60° C.
  2. waitcontinued for 3 days
  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
  10. customafter purification on silica (ethyl acetate/heptane 1:1

Sources & evidence

ORD record
ord-7880aa0c47d4481d95d086ae0fc21195
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

Loading…