Phosphorus pentachloride → HCID 86734068, compound

HRID 1287584Notes

Reaction equation

HRID 1287584 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([OH:18])=[C:13]([N:19]=O)[CH:12]=[CH:11]2>CCCCCC>[Cl:7][C:8]1[CH:17]=[CH:16][C:15]([C:14]([Cl:2])=[O:18])=[C:10]([CH:9]=1)/[CH:11]=[CH:12]\[C:13]#[N:19]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 21505309HCID 21505309, compound

Product 1

HCID 86734068HCID 86734068, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a rapidly stirring suspension of phosphorus pentachloride, 68.0 g, 0.326 mole in dry hexane (1.6 liters) is added 78.03 g (0.322 mole) of 6-chloro-2-nitroso-1-naphthol (I). The mixture is stirred at room temperature for 3 hours, the refluxed for 2 hours. The warm solution is then decanted and the residue in the reaction vessel refluxed for another hour with 1.0 liter of dry hexane. The hexane extracts are combined and evaporated to dryness. Yield: 75.0 g semi-solid brown residue. This crude product is recrystallized by taking it up in 2.0 liters of hot hexane, evaporating the solution down to a minimum volume (ca 300 ml) and cooling in an ice-water bath. Yield 31.0 g (42.59%).

Workup

  1. stirringThe mixture is stirred at room temperature for 3 hours
  2. temperaturethe refluxed for 2 hours
  3. customThe warm solution is then decanted
  4. temperaturethe residue in the reaction vessel refluxed for another hour with 1.0 liter of dry hexane
  5. customevaporated to dryness
  6. customThis crude product is recrystallized
  7. customevaporating the solution down to a minimum volume (ca 300 ml)
  8. temperaturecooling in an ice-water bath

Sources & evidence

ORD record
ord-f1f84ef93788418a83875c3acbcfc734
Source dataset
uspto-grants-1976_10
Patent number
US03985731

Reaction notes

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