Phosphorus pentachloride → HCID 20563848, compound

HRID 848647Notes

Reaction equation

HRID 848647 reaction equation
[Cl:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]([S:12]([O-])(=[O:14])=[O:13])[C:5]([CH3:11])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[K+].P(Cl)(Cl)(Cl)(Cl)[Cl:21]>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]([S:12]([Cl:21])(=[O:14])=[O:13])[C:5]([CH3:11])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 20563822HCID 20563822, compound

Product 1

HCID 20563848HCID 20563848, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Sixty grams of potassium 4-chloro-3,5-dinitro-o-toluenesulfonate, 70 grams of phosphorus pentachloride and 120 ml of phosphorus oxychloride are mixed and refluxed for 3 hours. The mixture is filtered to remove some insoluble solid. The filtrate is carefully poured into water at 20° C. to 30° C. The precipitated solid is collected and dissolved in 500 ml. of benzene. The benzene solution is washed with water and then dried over MgSO4. After removing the magnesium sulfate, the benzene is concentrated to 100 ml. and 400 ml. of hexane added. The precipitated solid is collected and recrystallized from 300 ml. hexane and 100 ml. of benzene to yield 50 grams of solid with melting point 105° C. to 107° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe mixture is filtered
  3. customto remove some insoluble solid
  4. additionThe filtrate is carefully poured into water at 20° C. to 30° C
  5. customThe precipitated solid is collected
  6. dissolutiondissolved in 500 ml
  7. washThe benzene solution is washed with water
  8. dry with materialdried over MgSO4
  9. customAfter removing the magnesium sulfate
  10. concentrationthe benzene is concentrated to 100 ml
  11. additionof hexane added
  12. customThe precipitated solid is collected
  13. customrecrystallized from 300 ml

Sources & evidence

ORD record
ord-17401b870a3e445f8a870e5eba65c181
Source dataset
uspto-grants-1981_10
Patent number
US04297127

Reaction notes

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