Water → 139393-89-8

HRID 2081530

Reaction equation

HRID 2081530 reaction equation
[C:1]([C:3]1[C:4](=O)[NH:5][C:6]([CH3:11])=[C:7]([CH2:9][CH3:10])[CH:8]=1)#[N:2].P(Cl)(Cl)(Cl)(Cl)[Cl:14].O>CCCCCC>[Cl:14][C:4]1[C:3]([C:1]#[N:2])=[CH:8][C:7]([CH2:9][CH3:10])=[C:6]([CH3:11])[N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24819Phosphorus pentachlorideHCID 102411095-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 10103778139393-89-8

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

3-Cyano-5-ethyl-6-methyl-2-(1H)-pyridinone (22.9 g, .141 mol) and phosphorus pentachloride (33.1 g, 0.159 mol) were intimately mixed and heated at 110°-120° C. for one hour. The liquified solids were poured onto crushed ice and water and the semi-solid was extracted into chloroform. This extract was washed with water, saturated aqueous NaHCO3, dried (Na2SO4), filtered and evaporated. This amber oil was dissolved in hexane and the insoluble material was removed when filtered through a pad of charcoal. Removal of the solvent gave a light yellow oil which solidified (17.7 g). Trituration of this solid with cold hexane yielded pure product, m.p. 63°-64° C.

Workup

  1. temperatureheated at 110°-120° C. for one hour
  2. additionThe liquified solids were poured
  3. extractionthe semi-solid was extracted into chloroform
  4. washThis extract was washed with water, saturated aqueous NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThis amber oil was dissolved in hexane
  9. customthe insoluble material was removed when
  10. filtrationfiltered through a pad of charcoal
  11. customRemoval of the solvent
  12. customgave a light yellow oil which

Sources & evidence

ORD record
ord-6f9963762328474d8a3df7df7c79e040
Source dataset
uspto-grants-1993_02
Patent number
US05185251

Linked notes

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