Potassium Iodide → HCID 19603707, compound

HRID 1604654Notes

Reaction equation

HRID 1604654 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]4[S:21][CH:22]=[C:23]([CH2:25]Cl)[N:24]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C-:27]#[N:28].[Na+].[I-].[K+]>CO>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]4[S:21][CH:22]=[C:23]([CH2:25][C:27]#[N:28])[N:24]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8929Sodium CyanideHCID 19603744HCID 19603744, compound

Product 1

HCID 19603707HCID 19603707, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-tert-butyl-2-{5-{[4-(chloromethyl)thiazol-2-yl]methyl}benzofuran-2-yl}thiazole (0.46 g) , sodium cyanide (0.22 g) and potassium iodide (0.19 g) in methanol (10 ml) was stirred under reflux for 21 hours. After being cooled, the mixture poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and toluene (1:20). The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-{5-{[4-(cyanomethy)thiazol-2-yl]methyl}benzofuran-2-yl}thiazole (0.19 g).

Workup

  1. temperatureunder reflux for 21 hours
  2. temperatureAfter being cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in reduced pressure
  7. customto give a syrup
  8. washeluted with a mixture of ethyl acetate and toluene (1:20)
  9. additionThe fractions containing object compound
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f02ba9de3e6484ca5e931342c50f3e3
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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