Potassium Iodide → HCID 19092824, compound

HRID 487691Notes

Reaction equation

HRID 487691 reaction equation
[CH2:1]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:29]Cl)=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C-:31]#[N:32].[Na+].[I-].[K+]>CO.[Cl-].[Na+].O>[CH2:1]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:29][C:31]#[N:32])=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 8929Sodium CyanideHCID 19092711HCID 19092711, compound

Product 1

HCID 19092824HCID 19092824, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4-hexyl-2-[5-(2-chloromethylphenylmethoxy)benzofuran-2-yl]thiazole (0.80 g), sodium cyanide (0.16 g) and potassium iodide (0.13 g) in methanol (10 ml) was refluxed for 2 hours. After being cooled, the mixture was poured into brine, extracted with ethyl acetate, dried over magnesium sulfate and concentrated in reduced pressure. The resulting residue was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and chloroform (1:33). The fractions containing object compound were combined and concentrated under reduced pressure to give an oil of 4-hexyl-2-[5-(2-cyanomethylphenylmethoxy)benzofuran-2-yl]thiazole (0.66 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter being cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in reduced pressure
  6. washeluted with a mixture of ethyl acetate and chloroform (1:33)
  7. additionThe fractions containing object compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3d650e05c77490389696557f2a498c8
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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