Ethyl Acetate → HCID 22662796, compound

HRID 392361

Reaction equation

HRID 392361 reaction equation
[F-:1].[K+].C1OCCOCCOCCOCCOCCOC1.Cl[C:22]1[N:27]=[C:26]([C:28]#[N:29])[CH:25]=[N:24][CH:23]=1.C(OCC)(=O)C>C(#N)C.C1(C)C=CC=CC=1.O>[F:1][C:22]1[N:27]=[C:26]([C:28]#[N:29])[CH:25]=[N:24][CH:23]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 2855718-Crown-6HCID 813036-Chloropyrazine-2-carbonitrileHCID 522689Potassium Fluoride

Product 1

HCID 22662796HCID 22662796, compoundYield 49.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent2×

Procedure

In a mixture of 140 ml of acetonitrile and 280 ml of toluene were suspended 58 g of potassium fluoride (spray-dried) and 8.7 g f 18-crown-6-ether. After heating the suspension under reflux for one hour in an atmosphere of nitrogen gas, the acetonitrile and toluene were distilled off under atmospheric pressure. The residue thus obtained was suspended in 280 mL of acetonitrile, 23 g of 6-chloro-2-pyrazinecarbonitrile synthesized according to the method described in Acta Poloniae Pharmaceutica, Vol. 33, Pages 153-161 (1976) was added, and the mixture thus obtained was heated under reflux for one hour in an atmosphere of nitrogen. The reaction mixture was cooled to room temperature, 280 mL of ethyl acetate and 280 mL of water were added, and the organic layer was separated. The organic layer thus obtained was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was distilled off under a reduce pressure. The residue was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=10:1] to obtain 10 g of 6-fluoro-2-pyrazinecarbonitrile as a white-colored solid product.

Workup

  1. temperatureAfter heating the suspension
  2. temperatureunder reflux for one hour in an atmosphere of nitrogen gas
  3. distillationthe acetonitrile and toluene were distilled off under atmospheric pressure
  4. customThe residue thus obtained
  5. additionwas added
  6. customthe mixture thus obtained
  7. temperaturewas heated
  8. temperatureunder reflux for one hour in an atmosphere of nitrogen
  9. customthe organic layer was separated
  10. customThe organic layer thus obtained
  11. washwas washed successively with water and saturated aqueous solution of sodium chloride
  12. dry with materialdried on anhydrous magnesium sulfate
  13. distillationthe solvent was distilled off under a reduce pressure
  14. customThe residue was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=10:1]

Sources & evidence

ORD record
ord-5c6ed00921bc476eb4b71e438687f8ad
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Linked notes

Loading…