Phosphorus pentachloride → HCID 22617176, compound

HRID 843371Notes

Reaction equation

HRID 843371 reaction equation
[Cl:1][C:2]([F:26])([F:25])[C:3]([F:24])([F:23])[C:4]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[N+:20]([O-:22])=[O:21])=O.P(Cl)(Cl)(Cl)(Cl)[Cl:28].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]([F:26])([F:25])[C:3]([F:24])([F:23])[C:4]([Cl:28])=[N:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 22617147HCID 22617147, compound

Product 1

HCID 22617176HCID 22617176, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.41 g (1.0 mmol) of 3-chloro-N-(2,6-dinitro-4-trifluoromethylphenyl)-2,2,3,3-tetrafluoropropionamide, 0.31 g (1.5 mmol) of phosphorous pentachloride, and 2 ml of toluene was heated under reflux for 6 hours. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 3-chloro-N-(2,6-dinitro-4-trifluoromethylphenyl)-2,2,3,3-tetrafluoropropionimidoyl chloride.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-314d8f1bb8024b88b05e84bfdaffa1e5
Source dataset
uspto-grants-2002_04
Patent number
US06376710B2

Reaction notes

Loading…