Phosphorus trichloride → 4-Chloro-6-ethyl-3-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine

HRID 968037Notes

Reaction equation

HRID 968037 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N+:5]([O-])=[C:4]([O:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[C:3]=1[CH3:21].P(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([O:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[C:3]=1[CH3:21]

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 219123464-Chloro-6-ethyl-3-methyl-2-(2,4,6-trimethyl-phenoxy)pyridine 1-oxide

Product 1

HCID 219123174-Chloro-6-ethyl-3-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-Chloro-6-ethyl-3-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine 1-oxide in methylene chloride was added PCl3 and the resulting mixture was heated at reflux for 20 min, cooled to rt. The mixture was concentrated to dryness. The residue was worked-up using standard procedure to give the title compound. After silica gel purification, the title compound was prepared as a white solid, mp. 42-44° C. Anal. For C17H20ClNO calc. C. 70.46; H, 6.96; N, 4.83; found, C, 70.35; H, 7.13; N, 4.58.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 20 min
  3. concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-5fe4a22861304a17b651fbbac11f79d9
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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