Phosphorus pentachloride → N-((5-bromo-2-chloropyridin-3-yl)chloromethylene)-2,3-dichlorobenzenamine

HRID 1518511Notes

Reaction equation

HRID 1518511 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])=O)[C:5]([Cl:8])=[N:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:21]>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([Cl:21])=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 56162074HCID 56162074, compound

Product 1

HCID 86616060N-((5-bromo-2-chloropyridin-3-yl)chloromethylene)-2,3-dichlorobenzenamineYield 96.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a slurry of 5-bromo-2-chloro-N-(2,3-dichlorophenyl)pyridine-3-carboxamide (0.75 g, 1.97 mmol) in benzene was added phosphorous pentachloride (0.5 g, 2.365 mmol) and the mixture heated to reflux. After 1.5 hours, the resulting solution was concentrated to provide 0.76 g of N-((5-bromo-2-chloropyridin-3-yl)chloromethylene)-2,3-dichlorobenzenamine as an off white solid. This material was used directly in the next reaction as is.

Workup

  1. temperaturethe mixture heated to reflux
  2. concentrationthe resulting solution was concentrated

Sources & evidence

ORD record
ord-2346a15fc24548c49a256d1c0c1933d0
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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