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

HRID 253957Notes

Reaction equation

HRID 253957 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-0d2f3a612e3a4556a5790d9d397c5eec
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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