Phosphorus oxychloride → 2-Chloro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-pyridine-3-carbonitrile

HRID 2293472Notes

Reaction equation

HRID 2293472 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[C:11]([C:15]#[N:16])=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:12]1[C:11]([C:15]#[N:16])=[CH:10][C:9]([C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 154085741,2-Dihydro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrile

Product 1

HCID 544469792-Chloro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-pyridine-3-carbonitrile

Procedure

A solution of 6-(4-fluorophenyl)-1,2-dihydro-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrile (Example 1, Step 5) (3.7 g, 0.011 mole) in phosphorus oxychloride (45 ml) was stirred at 100° C. for 20 hours. After evaporation of the phosphorus oxychloride the residue was purified by silica gel chromatography and recrystallized from ethyl acetate-hexane.

Workup

  1. customAfter evaporation of the phosphorus oxychloride the residue
  2. customwas purified by silica gel chromatography
  3. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b1436579b6ba44a4a9cc7739f8a65b33
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

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