Phosphorus trichloride → HCID 20382053, compound

HRID 1448141Notes

Reaction equation

HRID 1448141 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:6]=[N+:7]([O-])[CH:8]=[CH:9][C:10]=1[N+]([O-])=O.P(Cl)(Cl)[Cl:20]>C(Cl)(Cl)Cl>[Cl:20][C:10]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:4][C:3]1[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 112309183-(2-Chlorophenoxy)-4-nitro-1-oxo-1lambda~5~-pyridine

Product 1

HCID 20382053HCID 20382053, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4.9 g of 3-(o-chlorophenoxy)-4-nitropyridine N-oxide in 200 ml of chloroform is cooled to -5° C. and a large excess of phosphorous trichloride is added. The mixture is stirred 1 hour at 0° C. and slowly warmed to 25° C. The solution is refluxed 1 hour, cooled, concentrated at reduced pressure and dissolved in 100 ml of dichloromethane. The solution is washed with 50 ml of ice-cold concentrated ammonium hydroxide. The solution is dried over anhydrous MgSO4, filtered, concentrated at reduced pressure and distilled to yield 4-chloro-3-(o-chlorophenoxy)pyridine; bp 103°-105° C. at 0.1 mm.

Workup

  1. temperatureslowly warmed to 25° C
  2. temperatureThe solution is refluxed 1 hour
  3. temperaturecooled
  4. concentrationconcentrated at reduced pressure
  5. dissolutiondissolved in 100 ml of dichloromethane
  6. washThe solution is washed with 50 ml of ice-cold concentrated ammonium hydroxide
  7. dry with materialThe solution is dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated at reduced pressure
  10. distillationdistilled

Sources & evidence

ORD record
ord-90c42c9778a147b591befbbccd414c48
Source dataset
uspto-grants-1979_12
Patent number
US04179563

Reaction notes

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