Hydrochloric Acid → HCID 178423829, compound

HRID 1377634Notes

Reaction equation

HRID 1377634 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11](=O)[CH3:12])[C:9]#[N:10])=[CH:4][CH:3]=1.C(O)C.C(O[CH:20](OCC)[CH2:21][NH:22][NH2:23])C.Cl>O1CCOCC1.C(OCC)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:11]([CH3:12])=[N:23][N:22]3[CH:21]=[CH:20][NH:10][C:9]=23)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 322952(2,2-Diethoxyethyl)hydrazineHCID 1242431327243-91-0

Product 1

HCID 178423829HCID 178423829, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.7 g of 2-(4-methylphenyl)-3-oxo-butyronitrile, 20 ml of ethanol and 1.5 g of 2,2-diethoxyethylhydrazine was heated under reflux for 7 hours. At the end of this time, 30 ml of 4N hydrogen chloride in dioxane were added, and then the whole mixture was heated under reflux for a further 30 minutes. After the mixture had been cooled, diethyl ether was added to precipitate crystals. These were collected by filtration and partitioned between ethyl acetate and dilute aqueous ammonia. The organic phase was separated, washed with water and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to leave a residue, which was recrystallized from a mixture of ethyl acetate and hexane, to give 1.5 g of the title compound. The physical and chemical properties of this compound were the same as those of the compound prepared as described in Example 36.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. temperaturethe whole mixture was heated
  4. temperatureunder reflux for a further 30 minutes
  5. temperatureAfter the mixture had been cooled
  6. customto precipitate crystals
  7. filtrationThese were collected by filtration
  8. custompartitioned between ethyl acetate and dilute aqueous ammonia
  9. customThe organic phase was separated
  10. washwashed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was then removed by distillation under reduced pressure
  13. customto leave a residue, which
  14. customwas recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b6cb166493584139a8404037f923915a
Source dataset
uspto-grants-1997_09
Patent number
US05665752

Reaction notes

Loading…