Benzonitrile → HCID 178471717, compound

HRID 1847214Notes

Reaction equation

HRID 1847214 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn](Cl)(Cl)Cl.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=[O:17].C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[CH2:21]([O:20][C:14](=[O:19])[C:15](=[C:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:16](=[O:17])[CH3:18])[CH3:22]

Participants

6

Reactant 4

HCID 7505BenzonitrileHCID 8868Ethyl AcetoacetateHCID 24287Tin tetrachlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178471717HCID 178471717, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of the benzonitrile (40 g, 388.3 mmol) in benzene (600 mL) were added SnCl4 (44.75 mL, 388.3 mmol) and ethyl acetoacetate (49.1 mL, 388.3 mmol) at r.t. with stirring. The mixture was stirred at r.t. for 40 min, and was then refluxed with stirring for 2 h. After cooling to r.t. sat. NaHCO3 solution (200 mL) was added, and the mixture extracted with EtOAc (4×200 mL). The combined organic phases were washed with sat. aq. NaCl solution and water, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel. Elution with 5-33% EtOAc/CH2Cl2 gave the title compound as a white solid (41.1 g): MS (m/z) 234.3 (M+1).

Workup

  1. stirringThe mixture was stirred at r.t. for 40 min
  2. temperaturewas then refluxed
  3. stirringwith stirring for 2 h
  4. additionwas added
  5. extractionthe mixture extracted with EtOAc (4×200 mL)
  6. washThe combined organic phases were washed with sat. aq. NaCl solution and water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel
  10. washElution with 5-33% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-f8206d6672204f06800b937fc68ee514
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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