Hydrochloric Acid → HCID 53646989, compound

HRID 1080564Notes

Reaction equation

HRID 1080564 reaction equation
[CH2:1]([C:5]1[CH:11]=[CH:10][C:8](N)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[ClH:12].N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[C:22](#[N:25])[CH:23]=[CH2:24]>CC(C)=O.O>[Cl:12][CH:23]([CH2:24][C:8]1[CH:10]=[CH:11][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:6][CH:7]=1)[C:22]#[N:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 76944-ButylanilineHCID 7855AcrylonitrileHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 53646989HCID 53646989, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent3×

Conditions

Temperature
10 °C

Procedure

One and a half moles (237 mL) of 4-n-butylaniline was dissolved in acetone (1500 mL). The solution was cooled to 10° C. and water (150 mL) and concentrated aqueous HCl (300 mL) were added. Sodium nitrite (69.0 g, 1.73 moles) in water (200 mL) was added dropwise to the cooled solution. The solution was adjusted to pH 4 by addition of solid sodium acetate. Acrylonitrile (148 mL, 2.25 moles) was added, followed by CuCl2 ·2H2O (38.4 g) in 50 mL H2O. The reaction mixture was heated to 40° C. and was stirred at this temperature for 3 h. The aqueous layer was extracted with ether. The combined organics were washed with water and saturated aqueous NaHCO3, were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was fractionally distilled at reduced pressure. The product was collected at 115°-130° C. @2 mm Hg, as 166.3 g (50% yield) of an orange oil.

Workup

  1. temperatureThe reaction mixture was heated to 40° C.
  2. extractionThe aqueous layer was extracted with ether
  3. washThe combined organics were washed with water and saturated aqueous NaHCO3
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. distillationThe residue was fractionally distilled at reduced pressure
  8. customThe product was collected at 115°-130° C. @2 mm Hg

Sources & evidence

ORD record
ord-8da3ebf843134347b36d086185022f93
Source dataset
uspto-grants-1996_12
Patent number
US05582814

Reaction notes

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