Potassium Cyanide → {4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl}acetonitrile

HRID 1727366Notes

Reaction equation

HRID 1727366 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[S:13][C:12]([CH2:14][CH3:15])=[N:11][C:10]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[CH:6]=[CH:5][N:4]=1.[C-:23]#[N:24].[K+].C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:23]([CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[S:13][C:12]([CH2:14][CH3:15])=[N:11][C:10]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[CH:6]=[CH:5][N:4]=1)#[N:24]

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 229326992-(Chloromethyl)-4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridine

Product 1

HCID 22932829{4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl}acetonitrileYield 49.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 5-(2-chloromethyl-4-pyridyl)-2-ethyl-4-(3-methylphenyl)-1,3-thiazole (0.40 g, 1.2 mmol), potassium cyanide (0.095 g, 1.5 mmol), 18-crown-6 (0.14 g, 0.51 mmol) in acetonitrile (5 mL) was heated under reflux for 6 hours. After cooling, an aqueous potassium carbonate solution was added, and extracted with ethyl acetate. The extracts were washed with brine, then, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1). The resulting crystal was washed with hexane-isopropyl ether to obtain a title compound (0.19 g, 48%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1)
  9. washThe resulting crystal was washed with hexane-isopropyl ether

Sources & evidence

ORD record
ord-9954aaac9d144b888f8d59be7e21fbfb
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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