Phosphorus oxychloride → HCID 22767844, compound

HRID 1606563Notes

Reaction equation

HRID 1606563 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:8]([NH2:10])=O.P(Cl)(Cl)(Cl)=O>C(N(CC)CC)C>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:8]#[N:10]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21401563HCID 21401563, compound

Product 1

HCID 22767844HCID 22767844, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(3-Trifluoromethylphenoxy) (4-chlorophenyl)acetamide, (33.0 g., 0.1 mole) is dissolved in 250 ml. of phosphorus oxychloride and triethylamine (22.2 g.) is added over a 45-minute period with stirring while maintaining the temperature of the solution at 0°-2°C. Over a period of an hour the temperature is allowed to rise to 25°C. and then the solution is heated under reflux for 30 minutes. The solution is concentrated in vacuo (about 200 mm.) to remove volatile products and excess phosphorus oxychloride. Toluene (150 ml.) and ice water (250 ml.) are added to the residue. The toluene layer is separated and the aqueous phase is extracted with 3 × 75 ml. of toluene. The toluene solutions are combined and extracted with 0.5 N sodium hydroxide and then with water. The toluene solvent is removed in vacuo and the residue is distilled in vacuo (0.3 mm.). (3-Trifluoromethylphenoxy) (4-chlorophenyl)acetonitrile (27.6 g.) boiling at 144°-145°C. is obtained.

Workup

  1. temperaturewhile maintaining the temperature of the solution at 0°-2°C
  2. waitOver a period of an hour the temperature is allowed
  3. customto rise to 25°C.
  4. temperaturethe solution is heated
  5. temperatureunder reflux for 30 minutes
  6. concentrationThe solution is concentrated in vacuo (about 200 mm.)
  7. customto remove volatile products and excess phosphorus oxychloride
  8. additionToluene (150 ml.) and ice water (250 ml.) are added to the residue
  9. customThe toluene layer is separated
  10. extractionthe aqueous phase is extracted with 3 × 75 ml
  11. extractionextracted with 0.5 N sodium hydroxide
  12. customThe toluene solvent is removed in vacuo
  13. distillationthe residue is distilled in vacuo (0.3 mm.)

Sources & evidence

ORD record
ord-9a527ee6d6894ccc8cca7893d713513e
Source dataset
uspto-grants-1976_04
Patent number
US03953465

Reaction notes

Loading…