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

HRID 2308017Notes

Reaction equation

HRID 2308017 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 titel 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-35f8bc73312846ee89670dd01a2e1479
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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