Potassium Cyanide → HCID 19092790, compound

HRID 487682Notes

Reaction equation

HRID 487682 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]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27]Cl)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C-:29]#[N:30].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1.O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][C:29]#[N:30])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 190928204-Tert-butyl-2-[5-(2-chloromethylphenylmethoxy)benzofuran-2-yl]thiazole

Product 1

HCID 19092790HCID 19092790, compoundYield 85.7%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-(2-chloromethylphenylmethoxy)benzofuran-2-yl]thiazole (0.8 g), potassium cyanide (0.25 g) and Adogen 464 ((Aldrich phase transfer) one drop) in a mixture of toluene (8 ml) and water (8 ml) was stirred under reflux for 4 hours. After being cooled, the organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated in reduced pressure. The resulting residue was subjected to column chromatography on silica gel and eluted with toluene. The fractions containing object compound were combined and concentrated under reduced pressure to give an oil of 4-tert-butyl-2-[5-(2-cyanomethylphenylmethoxy)benzofuran-2-yl]thiazole (0.67 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter being cooled
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in reduced pressure
  7. washeluted with toluene
  8. additionThe fractions containing object compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3828fde968884821bfc0bee25c42bbb0
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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