Phosphorus pentachloride → HCID 19892769, compound

HRID 893076Notes

Reaction equation

HRID 893076 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:13][CH2:12]2)=O)=[CH:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:15]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]([Cl:15])[CH:11]2[CH2:13][CH2:12]2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 14304481N-(6-Fluoro-3-pyridinyl)cyclopropanecarboxamide

Product 1

HCID 19892769HCID 19892769, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-fluoro-5-pyridyl)-cyclopropane carboxamide (2.0 g, 0.011 mol) was added portionwise to a stirred solution of phosphorus pentachloride (2.31 g, 0.011 mol) in dichloromethane (20 ml) under a nitrogen atmosphere at room temperature. After complete addition the mixture was stirred at room temperature for one hour and then heated at reflux for a further one hour. The reaction mixture was then evaporated under vacuum to gave N-(2-fluoro-5-pyridyl)-cyclopropylmethanimidoyl chloride (2.1 g, 96%) which was used in Stage 3 without further purification or characterisation.

Workup

  1. additionAfter complete addition the mixture
  2. temperatureheated
  3. temperatureat reflux for a further one hour
  4. customThe reaction mixture was then evaporated under vacuum

Sources & evidence

ORD record
ord-d6fe7a8b336f41a7af0aaaffb58258c7
Source dataset
uspto-grants-1992_06
Patent number
US05122529

Reaction notes

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