Phosphorus pentachloride → [Chloro(4-nitrophenyl)methylidene]propanedinitrile

HRID 227615Notes

Reaction equation

HRID 227615 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].O[C:8]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[C:9]([C:12]#[N:13])[C:10]#[N:11]>ClCCl>[Cl:2][C:8]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[C:9]([C:12]#[N:13])[C:10]#[N:11]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 858427932-[Hydroxy(4-nitrophenyl)methylene]malononitrile

Product 1

HCID 71441079[Chloro(4-nitrophenyl)methylidene]propanedinitrileYield 57.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of PCl5 (16.6 g, 80 mmol) in dichloromethane (500 mL) was added dropwise to a suspension of Example 96A (8.6 g, 40 mmol) in dichloromethane (80 mL). The resulting mixture was heated to reflux for 20 hours, cooled to room temperature, and concentrated. The residue was dissolved in a minimal amount of dichloromethane and filtered through a plug of silica gel. The plug was washed with dichloromethane and the filtrate was concentrated. The concentrate was recrystallized from dichloromethane/hexanes to provide 5.4 g (57% yield) of the desired product. Rf=0.7 (5% methanol/dichloromethane).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 20 hours
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in a minimal amount of dichloromethane
  5. filtrationfiltered through a plug of silica gel
  6. washThe plug was washed with dichloromethane
  7. concentrationthe filtrate was concentrated
  8. customThe concentrate was recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-09c33b8b83b344fcabafc0c0088c590b
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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