Phosphorus pentachloride → HCID 14328051, compound

HRID 893074Notes

Reaction equation

HRID 893074 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([CH:12]2[CH2:14][CH2:13]2)=O)=[CH:5][N:4]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:16]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]([Cl:16])[CH:12]2[CH2:14][CH2:13]2)=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 86308N-(6-methoxypyridin-3-yl)cyclopropanecarboxamide

Product 1

HCID 14328051HCID 14328051, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide (5.0 g, 0.026 mol) was added portionwise to stirred solution of phosphorus pentachloride (5.42 g, 0.026 mol) in dichloromethane (25 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 give a solid product which was washed with diethyl ether (50 ml) and air dried to give N-(2-methoxy-5-pyridyl)-cyclopropylmethanimidoyl chloride as the hydrochloride salt (6.2 g, 97%) 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
  5. customto give a solid product which
  6. washwas washed with diethyl ether (50 ml) and air
  7. customdried

Sources & evidence

ORD record
ord-049bb2f932d54a5783f6a2f840c566cf
Source dataset
uspto-grants-1992_06
Patent number
US05122529

Reaction notes

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