Hydrochloric Acid → HCID 12356700, compound

HRID 1781496Notes

Reaction equation

HRID 1781496 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCN2C(=NCCC2)CC1.[C:27]([O:31][CH2:32][CH3:33])(=[O:30])[CH:28]=[CH2:29].Cl>C(O)C>[C:8]([C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:29][CH2:28][C:27]([O:31][CH2:32][CH3:33])=[O:30])#[N:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6837DiphenylacetonitrileHCID 8821Ethyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 12356700HCID 12356700, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of diphenylacetonitrile (28 g) in ethanol (100 ml) were added DBU (6 ml) and ethyl acrylate (30 ml), and the mixture was heated and stirred at 80° C. for 16 hours. After cooling, 2N-hydrochloric acid (200 ml) was added and the mixture was extracted with isopropyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude crystal crop was recrystallized from hexaneisopropyl ether to provide the title compound (34 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with isopropyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude crystal crop was recrystallized from hexaneisopropyl ether

Sources & evidence

ORD record
ord-45500bc5d2b740f7ad9d689e7536b18c
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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