Phosphorus pentachloride → HCID 92004511, compound

HRID 1287583Notes

Reaction equation

HRID 1287583 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([N:19]=O)=[C:15]2[OH:18])=[CH:10][CH:9]=1>CCCCCC>[Cl:7][C:8]1[CH:9]=[CH:10][C:11](/[CH:12]=[CH:13]\[C:14]#[N:19])=[C:16]([C:15]([Cl:2])=[O:18])[CH:17]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 215053107-Chloro-2-nitrosonaphthalen-1-ol

Product 1

HCID 92004511HCID 92004511, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a rapidly stirring suspension of phosphorus pentachloride (150.0 g) in dry hexane (2.6 liters) is added 156.4 g (0.72 mole) of 7-chloro-2-nitroso-1-naphthol (VI). The mixture is stirred at room temperature for 1 hour after which it is refluxed for 2 hours. The hexane solution is decanted while hot, 2.0 liters of dry hexane are added to the residue in the flask, and refluxed for another hour. The hexane solution is decanted, combined with the first hexane extract and evaporated to dryness. Yield: 100 g, semi-solid dark brown residue. The crude product is extracted with 2.0 liters of hot dry hexane. The hot supernatant solution is decanted from the tarry residue at the bottom of the flask, concentrated to a volume of 700 ml and cooled in an ice bath. Repeated extractions of the original residue and tarry material are done with a total of 3.0 liters of hexane. All of the extracts are concentrated, cooled in an ice bath, and the product filtered off and dried. Total yield: 51.1 g (31.4%), mp 71°-74°.

Workup

  1. stirringThe mixture is stirred at room temperature for 1 hour after which it
  2. temperatureis refluxed for 2 hours
  3. customThe hexane solution is decanted while hot, 2.0 liters of dry hexane
  4. additionare added to the residue in the flask
  5. temperaturerefluxed for another hour
  6. customThe hexane solution is decanted
  7. extractionextract
  8. customevaporated to dryness
  9. extractionThe crude product is extracted with 2.0 liters of hot dry hexane
  10. customThe hot supernatant solution is decanted from the tarry residue at the bottom of the flask
  11. concentrationconcentrated to a volume of 700 ml
  12. temperaturecooled in an ice bath
  13. extractionextractions of the original residue and tarry material
  14. concentrationAll of the extracts are concentrated
  15. temperaturecooled in an ice bath
  16. filtrationthe product filtered off
  17. customdried

Sources & evidence

ORD record
ord-6b6df0847dae42ef9b38d8a2d8b703ea
Source dataset
uspto-grants-1976_10
Patent number
US03985731

Reaction notes

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