Potassium Cyanide → HCID 20092979, compound

HRID 274579Notes

Reaction equation

HRID 274579 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:6][N:5]=[CH:4][N:3]=1.[C-:15]#[N:16].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[C:15]([C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:6][N:5]=[CH:4][N:3]=1)#[N:16]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 2009303235202-29-0

Product 1

HCID 20092979HCID 20092979, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-5-(p-tolyl)pyrimidine (7.4 g, 36 mmol), potassium cyanide (4.74 g, 72 mmol) and 18-crown-6 ether (0.48 g, 2 mmol) in acetonitrile (130 ml) was heated under reflux for 17 hours. After removal of insoluble materials by filtration from the reaction mixture, the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel to give crystals. Recrystallization from ethyl acetate-hexane afforded pale yellow needles (4.17 g, 59%), m.p. 107°-109° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hours
  3. customAfter removal of insoluble materials
  4. filtrationby filtration from the reaction mixture
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe residue was purified by column chromatography on silica gel
  7. customto give crystals
  8. customRecrystallization from ethyl acetate-hexane afforded pale yellow needles (4.17 g, 59%), m.p. 107°-109° C.

Sources & evidence

ORD record
ord-4e3ac0425f334abfb729422afbe9f303
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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