Phosphorus oxychloride → HCID 23362616, compound

HRID 344800Notes

Reaction equation

HRID 344800 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20](O)[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].P(Cl)(Cl)([Cl:30])=O>>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([Cl:30])[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178443713HCID 178443713, compound

Product 1

HCID 23362616HCID 23362616, compoundYield 91%

Procedure

Then, 5 g (0.013 mole) of the obtained ethyl 2-(p-octyloxyphenyl)-4-hydroxypyrimidine-5-carboxylate was dissolved in 25 ml of phosphorus oxychloride, and the mixture was refluxed with heating for 3 hours. The excess phosphorus oxychloride was distilled under reduced pressure, and the residue was purified by silica gel chromatography (developing solvent: CHCl3) to give 4.9 g of ethyl 2-(p-octyloxyphenyl)-4-chloropyrimidine-5-carboxylate (yield: 91%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 3 hours
  3. distillationThe excess phosphorus oxychloride was distilled under reduced pressure
  4. customthe residue was purified by silica gel chromatography (developing solvent: CHCl3)

Sources & evidence

ORD record
ord-c7f17d2fdc6642cbafce66a320d7297a
Source dataset
uspto-grants-1991_10
Patent number
US05053507

Reaction notes

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