Potassium Cyanide → HCID 20080511, compound

HRID 1653812Notes

Reaction equation

HRID 1653812 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[C-:28]#[N:29].[K+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:28]#[N:29])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 20080510HCID 20080510, compound

Product 1

HCID 20080511HCID 20080511, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5 g of 4,5-Bis(4-methoxyphenyl)-2-(5-bromopentyl)oxazole in 23 cm3 of ethanol and 1.1 g of potassium cyanide dissolved in 9 cm3 of water are brought to reflux for 15 hours. After evaporation of the solvent, the organic/inorganic residue is dissolved in 40 cm3 of diethyl ether and 10 cm3 of water, and the ether phase is separated and washed with 10 cm3 of saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated to dryness. The viscous residue (4.4 g) is chromatographed on a column of useful diameter 2 cm containing 80 g of silica gel (50 to 200μ). The column is eluted with 1.2 liters of diazopropyl ether, collecting 50 cm3 fractions. The fractions emerging at between 0.2 and 1.2 liters are concentrated to dryness. 3.5 g (80%) of 6-[4,5-bis(4-methoxyphenyl)-2-oxazolyl]hexanenitrile are obtained in the form of a pale yellow oil.

Workup

  1. temperatureto reflux for 15 hours
  2. customAfter evaporation of the solvent
  3. dissolutionthe organic/inorganic residue is dissolved in 40 cm3 of diethyl ether
  4. custom10 cm3 of water, and the ether phase is separated
  5. washwashed with 10 cm3 of saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe viscous residue (4.4 g) is chromatographed on a column of useful diameter 2 cm
  10. additioncontaining 80 g of silica gel (50 to 200μ)
  11. washThe column is eluted with 1.2 liters of diazopropyl ether
  12. customcollecting 50 cm3 fractions
  13. concentrationare concentrated to dryness

Sources & evidence

ORD record
ord-cfce80739ea24865bed2e06ab21c10a9
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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