Phosphorus oxychloride → HCID 18937859, compound

HRID 357523Notes

Reaction equation

HRID 357523 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N+:6]([O-])[CH:7]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:7]1[N:6]=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 53766535HCID 53766535, compound

Product 1

HCID 18937859HCID 18937859, compound

Conditions

Temperature
25 °C

Procedure

199.9 g (0.79 mol) of diethyl 5-methylpyridine-2,3-dicarboxylate N-oxide were introduced a little at a time, in the course of 1 hour at from 60° to 70° C, into 1 l of phosphoryl chloride, and the mixture was refluxed for 5 hours. After cooling to 25° C., the reaction mixture was evaporated down under reduced pressure and the residue was taken up in methylene chloride. After filtering through a suction funnel containing silica gel and evaporating down, 148.2 g (69% of theory) of the title compound were obtained as a pale syrup, which subsequently solidified. Mp. 84°-86° C.

Workup

  1. customthe reaction mixture was evaporated down under reduced pressure
  2. filtrationAfter filtering through a suction funnel
  3. additioncontaining silica gel
  4. customevaporating down

Sources & evidence

ORD record
ord-5cd84da1a37949f7929bcb4149c4ed70
Source dataset
uspto-grants-1998_11
Patent number
US05840904

Reaction notes

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